CH267585A - Process for the preparation of the new a- (benzimidazyl- (2)) - B- (N-ethyl-benzimidazyl- (2)) - ethylene. - Google Patents
Process for the preparation of the new a- (benzimidazyl- (2)) - B- (N-ethyl-benzimidazyl- (2)) - ethylene.Info
- Publication number
- CH267585A CH267585A CH267585DA CH267585A CH 267585 A CH267585 A CH 267585A CH 267585D A CH267585D A CH 267585DA CH 267585 A CH267585 A CH 267585A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzimidazyl
- ethylene
- ethyl
- mol
- ethylating agent
- Prior art date
Links
- 239000005977 Ethylene Substances 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000012021 ethylating agents Substances 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 239000000344 soap Substances 0.000 claims description 4
- 235000005811 Viola adunca Nutrition 0.000 claims description 3
- 240000009038 Viola odorata Species 0.000 claims description 3
- 235000013487 Viola odorata Nutrition 0.000 claims description 3
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000012459 cleaning agent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000037213 diet Effects 0.000 claims 1
- 235000005911 diet Nutrition 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001556 benzimidazoles Chemical group 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000009994 optical bleaching Methods 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstelluni" des neuen a-[Benzimidazyl-(2)1-p9-[N-äthyl- benzimidazyl-(2)l-äthylens. Es wurde gefunden, dass man das neue a- [ B enzimidazyl- (2) ] -ss, - [N-äthyl -benzimidazy 1- (2) ]-äthylen herstellen kann, wenn man a,ss- Di-[benzimidazyl-(2)]-äthylen mit,
einer zur Bildung des Monoäthylsubstitutionsproduktes ausreichenden Menge eines Äthylierungsmit- tels behandelt.
Das als Ausgangsmaterial zu verwendende a,ss-Di-[benzimidazyl-(2)]-äthylen kann nach bekannten Verfahren, beispielsweise durch 1?msetzutig einer Säure der Formel HOOC-CH = CH-COOH mit, o-Phenylendiamin, hergestellt werden.
Die Ausführung des Verfahrens kann in der Weise erfolgen, dass man ein Xthylierungs- mittel, beispielsweise Äthylchlorid oder Di- äthylsulfat, auf eine Lösung des a,f-Di-[benz- imidazy 1- (2) ] -äthylens in der Wärme einwir ken lässt.
Auf 1 Mol des Ausgangsmaterials verwendet man dabei zweckmässig mehr als 1 Mol, aber vorteilhaft weniger als 2 --Hol, vor- zugsweise etwa 1,27 bis 1,5 Mol des Äthylie- rungsmit:tels. Da das als Ausgangsstoff zu be nützende Diimidazol in den meisten Lösungs mitteln schwer löslich ist, benützt man mit Vorteil Lösungen seiner leichter löslichen Al kalisalze, z. B. Lösungen derselben in Äthyl alkohol.
Die Umsetzung wird zweekmä.ssig beire Siedepunkt des Lösungsmittels, gegebe nenfalls unter Druck, vorgenommen. Je nach den gewählten Reaktionsbedingungen kann das so erhaltene a-[Benzimidazyl-(2)]-ss-[N- äthy 1-benzimidazyl- (2) ] -äthy len von wechseln den Mengen an Ausgangsmaterial oder N,N'- Disubstitutionsprodukt begleitet: sein.
Auf Grund seiner verschiedenen Löslichkeit kann das a-[Benzimidazyl-(2)]-fl-[N-äthyl-benz- imidazyl-(2) ]-äthylen ohne weiteres aus dem entstandenen Gemisch abgetrennt werden.
Das a-[Benzimidazyl-(2) ] ss [N-äthyl-benz- imidazyl-(2)]-äthylen bildet ein hellgelbes Pulver, dessen alkoholische Lösung blauviolett fluoresziert. Es besitzt Affinität zur Zellulose faser und kann als optisches Bleichmittel, z. B. für Zellulosematerialien, verwendet, werden, vorteilhaft in Kombination mit Reinigungs mitteln, wie Seifen oder Salzen von sulfonier- ten, am 2-Kohlenstoffatom durch höhere Al kylreste substituierten Benzimidazolen.
Beispiel: Zn einer Lösung von 7 Teilen Natrium in 600 Teilen absolutem Alkohol gibt man 26 Teile a,f-Di-[benzimidazyl-(2)]-ä.thylen. Man erhitzt unter Rückfluss zum Kochen und fügt im Laufe von 2 Stunden 17,4 Teile Diäthy 1- sulfat zur siedenden Lösung hinzu. Man rührt noch einige Zeit. bei Siedetemperatur und lässt dann erkalten, wobei sich etwas a,ss-Di-[N- äthyl-benzimidazyl- (2) ]-äthylen abscheidet, das abfiltriert wird.
Das Filtrat.wird inWasser gegossen, das abgeschiedene a-[Benzimidazyl- (2) ] - f - [ N - äthyl - benzimidazyl- (2) ] - äthylen wird abgetrennt, mit Wasser neutral gewa schen und getrocknet.
Es kann über das Hy- drochlorid oder durch Umkristallisieren aus alkoholischer Natriumhydroxydlösung rein er halten werden und bildet dann ein hellgelbes Pulver, dessen alkoholische Lösung blauviolett flixoresziert.
Die neue Base kann zum Beispiel wie folgt verwendet werden: Zu einer Lösung von 100 Teilen Seife in 200 Teilen Wasser gibt man bei 70 bis<B>800</B> C 0,01 bis 0,3 Teile a-[Benzimid- azyl-(2) ] -ss- [N-äthyl-benzimidazyl-(2) ] -äthy- len. Sobald eine homogene Lösung entstanden ist, wird erkalten gelassen. Man erhält ein sei fenartiges Präparat. Ein mit diesem Präparat gewaschenes Textilgut besitzt ein weisseres Aussehen als nur mit Seife allein gewaschenes Material.
Process for the preparation of the new a- [benzimidazyl- (2) 1-p9- [N-ethylbenzimidazyl- (2) 1-ethylene. It has been found that the new a- [benzimidazyl (2)] -ss, - [N-ethyl -benzimidazy 1- (2)] -ethylene can be produced if a, ss- di- [benzimidazyl- (2)] - ethylene with,
an amount of an ethylating agent sufficient to form the monoethyl substitution product.
The α, β-di- [benzimidazyl- (2)] -ethylene to be used as the starting material can be prepared by known processes, for example by using an acid of the formula HOOC-CH = CH-COOH with, o-phenylenediamine.
The process can be carried out in such a way that an ethylating agent, for example ethyl chloride or diethyl sulfate, is placed in a hot solution of a, f-di- [benzimidazy 1- (2)] -ethylene ken.
For 1 mole of the starting material, it is advisable to use more than 1 mole, but advantageously less than 2 mol, preferably about 1.27 to 1.5 moles of the ethylenic agent. Since the diimidazole to be used as a starting material is sparingly soluble in most solvents, it is advantageous to use solutions of its more soluble Al potassium salts, eg. B. Solutions of the same in ethyl alcohol.
The reaction is carried out two times at the boiling point of the solvent, if necessary under pressure. Depending on the reaction conditions chosen, the a- [benzimidazyl- (2)] - ss- [N-ethy 1-benzimidazyl- (2)] ethene obtained in this way can be accompanied by varying amounts of starting material or N, N'-disubstitution product : his.
Because of its different solubility, the a- [benzimidazyl- (2)] -fl- [N-ethyl-benzimidazyl- (2)] -ethylene can easily be separated from the resulting mixture.
The a- [benzimidazyl- (2)] ss [N-ethyl-benz- imidazyl- (2)] - ethylene forms a light yellow powder, the alcoholic solution of which fluoresces blue-violet. It has an affinity for cellulose fiber and can be used as an optical bleaching agent, e.g. B. for cellulose materials, are used, advantageously in combination with cleaning agents, such as soaps or salts of sulfonated, benzimidazoles substituted on the 2-carbon atom by higher alkyl radicals.
Example: 26 parts of a, f-di- [benzimidazyl- (2)] ethylene are added to a solution of 7 parts of sodium in 600 parts of absolute alcohol. The mixture is heated to the boil under reflux and 17.4 parts of diethyl sulfate are added to the boiling solution over the course of 2 hours. One stirs for a while. at boiling point and then allowed to cool, some α, β-di- [N-ethylbenzimidazyl- (2)] -ethylene separating out, which is filtered off.
The filtrate is poured into water, the precipitated a- [benzimidazyl- (2)] - f - [N - ethyl - benzimidazyl (2)] - ethylene is separated off, washed neutral with water and dried.
It can be obtained in pure form via the hydrochloride or by recrystallization from an alcoholic sodium hydroxide solution and then forms a light yellow powder, the alcoholic solution of which has a blue-violet fluorescence.
The new base can be used as follows, for example: 0.01 to 0.3 parts of a- [benzimidazyl] are added at 70 to 800 C to a solution of 100 parts of soap in 200 parts of water - (2)] -ss- [N-ethyl-benzimidazyl- (2)] -ethylene. As soon as a homogeneous solution has arisen, it is left to cool. A bee-like preparation is obtained. Textiles washed with this preparation have a whiter appearance than material washed with soap alone.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH263627T | 1947-03-19 | ||
| CH267585T | 1947-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267585A true CH267585A (en) | 1950-03-31 |
Family
ID=25730656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267585D CH267585A (en) | 1947-03-19 | 1947-03-19 | Process for the preparation of the new a- (benzimidazyl- (2)) - B- (N-ethyl-benzimidazyl- (2)) - ethylene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267585A (en) |
-
1947
- 1947-03-19 CH CH267585D patent/CH267585A/en unknown
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