CH295294A - Process for the preparation of a derivative of 4,4'-diaminostilbene-disulfonic acid- (2,2 '). - Google Patents
Process for the preparation of a derivative of 4,4'-diaminostilbene-disulfonic acid- (2,2 ').Info
- Publication number
- CH295294A CH295294A CH295294DA CH295294A CH 295294 A CH295294 A CH 295294A CH 295294D A CH295294D A CH 295294DA CH 295294 A CH295294 A CH 295294A
- Authority
- CH
- Switzerland
- Prior art keywords
- disulfonic acid
- parts
- preparation
- derivative
- diaminostilbene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007859 condensation product Substances 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 238000009994 optical bleaching Methods 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- -1 p-methoxybenzoyl Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Description
Verfahren zur Herstellung eines Derivates der 4,4'-Diaminostilben-disulfonsäure-(2,2'). Es wurde gefunden, dass man zu einem neuen Derivat der 4,4'-Diaminostilben-disul- fonsäure-(2,2') gelangt, wenn man auf 1 Mol des Kondensationsproduktes aus dem Dina- triumsalz der 4-[(p-Methoxybenzoyl)-amino]- ,r'-aminostilben-disulfonsäure-(2,2')
und Cya- nurchlorid 1 Mol Diäthanolamin einwirken lässt. Die Umsetzung kann z. B. in schwach alkalischer Lösung bei etwa 40 vorgenommen werden. .
Das neue Dinatriumsalz der 4- [ (p-Meth- oxybenzoyl) -amino] -4'- [2-chlor-4-(bis-fl-oxy- äthyl)-amino-1,3,5-triazyl-(6 )-amino] -stilben- disul:fonsäure-(2,2') der Formel
EMI0001.0027
bildet ein hellgelbes Pulver, das in Wasser löslich ist.
Es kann als optisches Bleichmittel verwendet werden. Zellulosematerial, das mit einer solchen Lösung behandelt worden ist, fluoresziert im ultravioletten Licht. bläulich. <I>Beispiel:
</I> Zu einer mit Natriumcarbonat alkalisch gestellten Lösung von 47,6 Teilen 84 /oiger 4-Amino-4'-nitro-stilben-@disulfonsäure- (2,2') in 300 Teilen Wasser und 300 Teilen Aceton wird bei 10-15 C eine Lösung von 20 Teilen 4-Methoxy-benzoylchlorid in 40 Teilen Aceton innerhalb von etwa 1 Stunde zugetropft. So bald das Ausgangsmaterial verschwunden ist, wird Natriiunchloridlösung zugefügt, das ab geschiedene Kondensationsprodukt abfiltriert, mit.
Natriumehloridlösung gewaschen und durch Eintragen in ein aus 500 Teilen Wasser, 30 Teilen Eisessig und 66 Teilen Eisen bestehendes Reduktionsgemisch redu ziert.
Aus dem mit Natriumcarbonat alkalisch gestellten Reduktionsgemenge wird das Dina- trzumsalz der entstandenen 4-[ (p-Methoxy- benzoyl) - amino] - 4' - aminostilben - disulfon- säure-(2,2') mit Natriumchlorid abgeschieden, filtriert, mit Natriumchloridlösung gewaschen und getrocknet.
5,5 Teile des erhaltenen Produktes werden in 100 Teilen Wasser gelöst und bei 0-5 C s@u einer feinen, durch Eintragen von 2 Teilen in 10 Teilen Aceton gelöstem Cyanurchlorid in ein aus 20 Teilen Eis und 20 Teilen Wasser bestehendes Gemisch erhaltenen Suspension zugetropft, wobei die Reaktionsmasse durch allmähliches Zugeben von 0,5 Teilen in 5 Teilen Wasser gelöstem Natriumcarbonat schwach sauer bis neutral gehalten wird. So bald das Ausgangsmaterial verschwunden ist, werden 3 Teile Diäthanolamin zugefügt,
die Temperatur innerhalb einer Stunde auf 40 C gesteigert und 5 Stunden bei dieser Tempera tur gehalten. Das 'entstandene Dinatri.iunsalz wird hierauf mit Natriuxnchlorid abgeschie den, filtriert, mit wässeriger Natriiunchlorid- lösung gewaschen und getrocknet. Es bildet ein hellgelbes Pulver, das in Wasser löslich ist und zum optischen Bleichen von Textil material verwendet werden kann.
Process for the preparation of a derivative of 4,4'-diaminostilbene-disulfonic acid- (2,2 '). It has been found that a new derivative of 4,4'-diaminostilbene-disulphonic acid- (2,2 ') is obtained if 1 mol of the condensation product from the dinatrium salt of 4 - [(p-methoxybenzoyl ) -amino] -, r'-aminostilbene-disulfonic acid- (2,2 ')
and cyanuric chloride allows 1 mol of diethanolamine to act. The implementation can e.g. B. be made in weakly alkaline solution at about 40. .
The new disodium salt of 4- [(p-methoxybenzoyl) -amino] -4'- [2-chloro-4- (bis-fl-oxy-ethyl) -amino-1,3,5-triazyl- (6 ) -amino] -stilbene disul: fonsäure- (2,2 ') of the formula
EMI0001.0027
forms a light yellow powder that is soluble in water.
It can be used as an optical bleach. Cellulosic material that has been treated with such a solution fluoresces in ultraviolet light. bluish. <I> example:
To a solution made alkaline with sodium carbonate of 47.6 parts of 84% 4-amino-4'-nitro-stilbene- @ disulfonic acid- (2.2 ') in 300 parts of water and 300 parts of acetone is added at 10 -15 C a solution of 20 parts of 4-methoxy-benzoyl chloride in 40 parts of acetone was added dropwise within about 1 hour. As soon as the starting material has disappeared, sodium chloride solution is added and the condensation product which has separated off is filtered off with.
Washed sodium chloride solution and reduced by introducing it into a reduction mixture consisting of 500 parts of water, 30 parts of glacial acetic acid and 66 parts of iron.
The dinatrium salt of the 4- [(p-methoxybenzoyl) -amino] -4'-aminostilbene-disulfonic acid- (2,2 ') formed is precipitated with sodium chloride from the reduction mixture made alkaline with sodium carbonate, filtered, with Washed sodium chloride solution and dried.
5.5 parts of the product obtained are dissolved in 100 parts of water and a fine suspension of cyanuric chloride, dissolved by introducing 2 parts in 10 parts of acetone, into a mixture consisting of 20 parts of ice and 20 parts of water is obtained at 0-5 C s @ u added dropwise, the reaction mass being kept slightly acidic to neutral by gradually adding 0.5 part of sodium carbonate dissolved in 5 parts of water. As soon as the starting material has disappeared, 3 parts of diethanolamine are added,
the temperature increased to 40 C within an hour and held at this tempera ture for 5 hours. The resulting disodium salt is then separated off with sodium chloride, filtered, washed with aqueous sodium chloride solution and dried. It forms a light yellow powder that is soluble in water and can be used for optical bleaching of textile material.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH295294T | 1949-10-28 | ||
| CH291791T | 1949-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH295294A true CH295294A (en) | 1953-12-15 |
Family
ID=25733137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH295294D CH295294A (en) | 1949-10-28 | 1949-10-28 | Process for the preparation of a derivative of 4,4'-diaminostilbene-disulfonic acid- (2,2 '). |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH295294A (en) |
-
1949
- 1949-10-28 CH CH295294D patent/CH295294A/en unknown
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