DE522082C - Process for the preparation of acidic wool dyes of the anthraquinone series - Google Patents
Process for the preparation of acidic wool dyes of the anthraquinone seriesInfo
- Publication number
- DE522082C DE522082C DEI38298D DEI0038298D DE522082C DE 522082 C DE522082 C DE 522082C DE I38298 D DEI38298 D DE I38298D DE I0038298 D DEI0038298 D DE I0038298D DE 522082 C DE522082 C DE 522082C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- parts
- anthraquinone series
- wool dyes
- dyes
- 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 9
- 210000002268 wool Anatomy 0.000 title claims description 6
- 230000002378 acidificating effect Effects 0.000 title claims description 3
- 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
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004327 boric acid Substances 0.000 claims description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- C09B1/48—Anthrimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung von sauren Wollfarbstoffen der Anthrachinonreihe Nach der deutschen Patentschrift 414 865 erhält man Wollfarbstoffe durch Sulfieren von Amino- oder Alkylaminodianthrachinonylaminen mittels Oleum bei An- oder Abwesenheit von Borsäure.Process for the preparation of acidic wool dyes of the anthraquinone series According to German Patent 414 865, wool dyes are obtained by sulfating of amino or alkylaminodianthraquinonylamines using oleum in the presence or absence of boric acid.
Es wurde nun gefunden, daß die Sulfierung dieser Dianthrachinonylaminderivate mit borsäurehaltigem Oleum wesentlich rascher erfolgt und zu leichter löslichen, wahrscheinlich höher sulfierten Produkten führt, welche für Färbereizwecke von besonderem Wert sind, wenn man sie bei Gegenwart von Ouecksilber, dessen Oxyden oder Salzen, vorzugsweise bei Temperaturen zwischen ungefähr i2o bis 15o° ausführt.It has now been found that the sulphonation of these dianthraquinonylamine derivatives with oleum containing boric acid takes place much more quickly and results in more easily soluble, probably higher sulfated products, which are of particular use for dyeing purposes Are of value if they are used in the presence of mercury, its oxides or salts, preferably carried out at temperatures between about 12o to 15o °.
Es war nicht vorauszusehen, daß das Ouecksilber oder seine Salze oder Oxyde unter diesen Bedingungen den Eintritt von Sulfogruppen erleichtern würde, ohne die gleichzeitige Bildung von Oxydationsprodukten zu begünstigen, wie dies bei Abwesenheit von Borsäure der Fall ist (s. z. B. Patentschrift 472 356, Beispiel 3).It was not foreseeable that the mercury or its salts or Oxides would facilitate the entry of sulfo groups under these conditions, without promoting the simultaneous formation of oxidation products, like this is the case in the absence of boric acid (see e.g. patent specification 472 356, example 3).
Beispiel i 5 Gewichtsteile 4-Amino-i # i'-dianthrachinonylamin werden in 75 Gewichtsteile Oleum von 270;o S03, das 2 Gewichtsteile Borsäure und o,i Gewichtsteil Hg0 gelöst (bzw. suspendiert) enthält, unter Rühren eingetragen und so lange auf 135 bis i4o° erhitzt, bis eine herausgenommene Probe in Wasser sehr leicht löslich geworden ist. Dies ist nach etwa 3'/, Stunden der Fall. Die abgekühlte Schmelze wird in 5oo Teile Wasser eingerührt, das mit etwas schwefliger Säure versetzt wurde, dann mit Zoo Teilen gesättigter Kochsalzlösung zum Sieden erhitzt, der abgeschiedene Farbstoff filtriert und mit verdünnter Kochsalzlösung neutral gewaschen.Example i 5 parts by weight of 4-amino-i # i'-dianthraquinonylamine become in 75 parts by weight of oleum of 270; o SO3, the 2 parts by weight boric acid and 0.1 part by weight Hg0 dissolved (or suspended) contains, entered with stirring and so long on 135 to 14o ° until a sample taken out is very easily soluble in water has become. This is the case after about 3½ hours. The cooled melt is stirred into 500 parts of water to which a little sulphurous acid has been added, then heated to the boil with zoo parts of saturated saline, the deposited Filtered dye and washed neutral with dilute sodium chloride solution.
Er färbt Wolle aus saurem Bade in klaren graublauen Tönen von hervorragenden Echtheitseigenschaften. Beispiel e io Gewichtsteile 4 # 4'-Diamino-i # i'-dianthrachinony lamin werden unter Rühren in i 5 o Gewichtsteilen Oleum von 27% S O3, in dem zuvor 4 Teile Borsäure aufgelöst und 0,2 Teile Hg0 suspendiert waren, gelöst und dann auf 135 bis 140° etwa 3 Stunden erhitzt. Die Schmelze wird nach dem Abkühlen in 8oo Teile Wasser eingerührt, das mit wenig schwefliger Säure versetzt war, sodann mit 6oo Teilen gesättigter Kochsalzlösung aufgekocht. Der abgeschiedene Farbstoff wird abfiltriert und mit verdünnter Kochsalzlösung neutral gewaschen.He dyes wool from an acid bath in clear gray-blue shades of excellent Authenticity properties. Example e 10 parts by weight of 4 # 4'-diamino-i # i'-dianthraquinony lamin are stirred in i 5 o parts by weight oleum of 27% SO3, in the previously 4 parts of boric acid were dissolved and 0.2 parts of Hg0 were suspended, and then dissolved heated to 135 to 140 ° for about 3 hours. After cooling, the melt is in 800 parts of water to which a little sulphurous acid was added, then stirred in boiled with 600 parts of saturated saline solution. The deposited dye is filtered off and washed neutral with dilute sodium chloride solution.
Das Produkt ist in Wasser wesentlich leichter löslich als der Farbstoff der Patentschrift 414 865, Beispiel i. Es färbt ungebeizte Wolle aus saurem Bade in kräftigen blaugrauen Tönen von hervorragenden Echtheitseigenschaften. .The product is much more soluble in water than the dye of patent 414 865, example i. It dyes unstained wool from an acid bath in strong blue-gray Tones with excellent fastness properties. .
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI38298D DE522082C (en) | 1929-06-07 | 1929-06-08 | Process for the preparation of acidic wool dyes of the anthraquinone series |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE349325T | 1929-06-07 | ||
| DEI38298D DE522082C (en) | 1929-06-07 | 1929-06-08 | Process for the preparation of acidic wool dyes of the anthraquinone series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE522082C true DE522082C (en) | 1931-03-30 |
Family
ID=31947502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI38298D Expired DE522082C (en) | 1929-06-07 | 1929-06-08 | Process for the preparation of acidic wool dyes of the anthraquinone series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE522082C (en) |
-
1929
- 1929-06-08 DE DEI38298D patent/DE522082C/en not_active Expired
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