DE1220438B - Process for the preparation of surface-active polyhydroxyalkylamines and their acid addition salts - Google Patents
Process for the preparation of surface-active polyhydroxyalkylamines and their acid addition saltsInfo
- Publication number
- DE1220438B DE1220438B DED38616A DED0038616A DE1220438B DE 1220438 B DE1220438 B DE 1220438B DE D38616 A DED38616 A DE D38616A DE D0038616 A DED0038616 A DE D0038616A DE 1220438 B DE1220438 B DE 1220438B
- Authority
- DE
- Germany
- Prior art keywords
- acid addition
- addition salts
- polyhydroxyalkylamines
- active
- preparation
- 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.)
- Pending
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
Description
Verfahren zur Herstellung von grenzflächenaktiven Polyhydroxyalkylaminen und deren Säureadditionssalzen Es ist bekannt, daß Alkylenoxyde in der Lage sind, Amine zu addieren, soweit letztere an Stickstoff gebundene Wasserstoffatome aufweisen.Process for the preparation of polyhydroxyalkyl surfactant amines and their acid addition salts It is known that alkylene oxides are capable of To add amines, as far as the latter have hydrogen atoms bound to nitrogen.
So können primäre Amine zwei, sekundäre Amine nur eine Hydroxyalkylgruppe aufnehmen, wobei Hydroxyalkylamine gebildet werden. Primary amines can be two, secondary amines only one hydroxyalkyl group take up, whereby hydroxyalkylamines are formed.
Auf dem Gebiet der grenzflächenaktiven Stoffe wurden bisher lediglich Alkylenoxyde mit kurzer Kohlenstoffkette, beispielsweise Äthylenoxyd oder Propylenoxyd, an hydrophobe Grundstoffe, wie Fettamine, angelagert, um diese wasserlöslich zu machen, also zur Bildung des hydrophilen Molekülanteils. In the area of surface-active substances, only Alkylene oxides with a short carbon chain, e.g. ethylene oxide or propylene oxide, attached to hydrophobic raw materials, such as fatty amines, to make them water-soluble make, i.e. to form the hydrophilic part of the molecule.
Es wurde nun gefunden, daß man grenzflächenaktive Polyhydroxyalkylamine der allgemeinen Formel in der Reinen Alkylrest mit 6 bis 18 Kohlenstoffatomen, R1 Wasserstoff oder einen niederen Alkylrest oder niederen Hydroxyalkylrest, R2 einen Hydroxyalkylrest oder einen Polyhydroxyalkanrest bedeutet, und deren Säureadditionssalze herstellen kann, wenn man in an sich bekannter Weise Hydroxyamine der allgemcinen Formel mit Alkylenoxyden der allgemeinen Formel in Dimethylformamid bei Temperaturen zwischen 20 und 150"C oder bei Mischbarkeit der Komponenten lösungsmittelfrei umsetzt und gegebenenfalls die erhaltenen Basen in ihre Säureadditionssalze überführt.It has now been found that surface-active polyhydroxyalkylamines of the general formula in which pure alkyl radical with 6 to 18 carbon atoms, R1 is hydrogen or a lower alkyl radical or lower hydroxyalkyl radical, R2 is a hydroxyalkyl radical or a polyhydroxyalkane radical, and acid addition salts thereof can be prepared if, in a manner known per se, hydroxyamines of the general formula with alkylene oxides of the general formula in dimethylformamide at temperatures between 20 and 150 ° C. or if the components are miscible in a solvent-free manner and, if appropriate, the bases obtained are converted into their acid addition salts.
Man läßt die Alkylenoxyde und die Hydroxyamine, in Dimethylformamid gelöst, bei Temperaturen zwischen 20 und 150"C aufeinander einwirken, vertreibt nach erfolgter Reaktion das Lösungsmittel im Vakuum und erhält als Rückstand die Polyhydroxyalkylamine. The alkylene oxides and the hydroxyamines are left in dimethylformamide dissolved, act on each other at temperatures between 20 and 150 "C, drives away after the reaction, the solvent in vacuo and the residue is obtained Polyhydroxyalkylamines.
Lassen sich Alkylenoxyde und Hydroxyamine bei erhöhter Temperatur unter starkem Rühren homogenisieren, wie dies beispielsweise beim Diäthanolamin der Fall ist, so ist es zweckmäßig, die Reaktion lösungsmittelfrei ablaufen zu lassen.Can alkylene oxides and hydroxyamines at elevated temperature Homogenize with vigorous stirring, as is the case with diethanolamine, for example is the case, it is expedient to allow the reaction to proceed without solvent.
Die Polyhydroxyalkylamine lassen sich sowohl durch anorganische als auch durch organische Säuren in die entsprechenden kationenaktiven Salze über-: führen, wodurch ihre Löslichkeit in Wasser gesteigert werden kann. The polyhydroxyalkylamines can be both by inorganic as also converted into the corresponding cationic salts by organic acids: lead, whereby their solubility in water can be increased.
Polyhydroxyalkylamine sind in der Lage, die Oberflächenspannung ihrer wäßrigen Lösungen bereits in geringen Konzentrationen stark herabzusetzen. Polyhydroxyalkylamines are able to reduce their surface tension greatly reduce aqueous solutions even in low concentrations.
Sie besitzen in wäßrigen Lösungen ein starkes Schaumvermögen. Die Schäume sind sehr beständig. Als Basen sind sie physiologisch stark wirksam. Sie eignen sich als Textilhilfs- und Waschmittel, als Emulgatoren und auf Grund ihrer physiologischen Wirksamkeit als Kosmetika und Pharmazeutika.They have a strong foaming power in aqueous solutions. the Foams are very durable. As bases, they have a strong physiological effect. she are suitable as textile auxiliaries and detergents, as emulsifiers and because of their physiological effectiveness as cosmetics and pharmaceuticals.
Die erfindungsgemäßen Verfahrensprodukte besitzen gegenüber bekannten Produkten ähnlicher Konstitution überlegene grenzflächenaktive Eigenschaften, was nachfolgend durch Bestimmung des Emulgiervermögens bewiesen wird. The process products according to the invention have compared to known Products of similar constitution superior surface-active properties what is subsequently proven by determining the emulsifying power.
Es wird das Emulgiervermögen von erfindungsgemäß hergestellten N-(2-Hydroxy-n-dodecyl)-diäthanolamin (A) mit dem von N-Dodecyldiäthanolamin (B) verglichen. Zu diesem Zweck wurde die mit der Zeit fortschreitende Phasentrennung einer Leinöl-Wasser-Emulsion bestimmt. Die Emulsionen bestehen aus 9,5 Gewichtsteilen Leinöl, 9,5 Gewichtsteilen Wasser und 0,65 Gewichtsteilen der zu prüfenden Substanzen. It becomes the emulsifying power of N- (2-hydroxy-n-dodecyl) diethanolamine prepared according to the invention (A) compared to that of N-dodecyl diethanolamine (B). For this purpose the phase separation of a linseed oil-water emulsion that progressed over time was determined. The emulsions consist of 9.5 parts by weight of linseed oil and 9.5 parts by weight of water and 0.65 parts by weight of the substances to be tested.
Die nachfolgende Tabelle zeigt das Prüfungsergebnis.
Es wird 1 Stunde auf 150"C erhitzt. Man destilliert anschließend im Ölpumpenvakuum. Sirup öse, farblöse F1üssigkeit,.~ die bei~2mmbei 203>C siedet.It is heated to 150 ° C. for 1 hour. It is then distilled in Oil pump vacuum. Syrup eyelet, colorless liquid, which boils at ~ 2mm at 203> C.
Ausbeute 900/o der Theorie.Yield 900 / o of theory.
Beispiel 2 N-Methyl-N-(2-hydroxyoctyl)-glucamin 2 g N-Methylglucamin werden in 5 com frisch destilliertem Dimethylformamid gelöst. Danach werden 1,3 g Octylenoxyd-1,2 hinzugegeben. Das Reaktionsgemisch wird 2 Stunden auf 75 0C erwärmt.Example 2 N-Methyl-N- (2-hydroxyoctyl) -glucamine 2 g of N-methylglucamine are dissolved in 5 com of freshly distilled dimethylformamide. Then 1.3 g of 1,2-octylene oxide are added. The reaction mixture is heated to 75 ° C. for 2 hours.
Nach dieser Zeit läßt man erkalten und fällt die Base mit Äther. Sie schmilzt bei 93 bis 93,5°C. Ausbeute 850/o der Theorie.After this time it is allowed to cool and the base is precipitated with ether. she melts at 93 to 93.5 ° C. Yield 850 / o of theory.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED38616A DE1220438B (en) | 1962-04-09 | 1962-04-09 | Process for the preparation of surface-active polyhydroxyalkylamines and their acid addition salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED38616A DE1220438B (en) | 1962-04-09 | 1962-04-09 | Process for the preparation of surface-active polyhydroxyalkylamines and their acid addition salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1220438B true DE1220438B (en) | 1966-07-07 |
Family
ID=7044228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED38616A Pending DE1220438B (en) | 1962-04-09 | 1962-04-09 | Process for the preparation of surface-active polyhydroxyalkylamines and their acid addition salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1220438B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4085144A (en) * | 1975-06-02 | 1978-04-18 | Sterling Drug Inc. | N,N'-Bridged-bis(2-alkyl-2-hydroxyethylamine) dioxides |
| US4328371A (en) * | 1980-12-15 | 1982-05-04 | Henkel Corporation | Alkylene oxide adducts of amino alcohols |
-
1962
- 1962-04-09 DE DED38616A patent/DE1220438B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4085144A (en) * | 1975-06-02 | 1978-04-18 | Sterling Drug Inc. | N,N'-Bridged-bis(2-alkyl-2-hydroxyethylamine) dioxides |
| US4328371A (en) * | 1980-12-15 | 1982-05-04 | Henkel Corporation | Alkylene oxide adducts of amino alcohols |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1445403A1 (en) | New sulfobetaines | |
| DE2730923A1 (en) | PROCESS FOR THE PREPARATION OF Aqueous FINE DISPERSES, STORAGE-STABLE SILICON OIL EMULSIONS | |
| EP0075065B1 (en) | Process for the preparation of quaternary ammonium compounds | |
| DE1923063A1 (en) | Process for the production of alpha-pyrrolidone | |
| DE1220438B (en) | Process for the preparation of surface-active polyhydroxyalkylamines and their acid addition salts | |
| DE634037C (en) | Process for the production of organic compounds with acidic, salt-forming groups | |
| DE2721626A1 (en) | COMPOUNDS OF THE N, N'-POLYOXIALKYLENE-BIS (PYRROLIDINONE-3-CARBONIC ACIDS) TYPE, METHOD FOR THEIR PRODUCTION AND THEIR USE | |
| DE552268C (en) | Process for the preparation of higher molecular oxyalkylamines | |
| DE1240872B (en) | Process for the production of water-soluble, capillary-active ampholytes that can be used as washing and cleaning agents and as foam stabilizers | |
| DE2725780C2 (en) | ||
| DE4238207A1 (en) | New quat. fatty acid poly:hydroxy:alkylamide(s) - useful in prodn. of antistatic agents for tissue and textile surfaces | |
| DE552758C (en) | Process for the production of wetting, cleaning and dispersing agents | |
| DE664425C (en) | Process for the production of oxidation products of high molecular weight amines | |
| AT158265B (en) | Process for the production of higher molecular weight quaternary ammonium salts. | |
| DE683801C (en) | Process for the preparation of substituted amides of fatty aromatic monocarboxylic acids | |
| DE611373C (en) | Process for the preparation of fatty acid derivatives | |
| DE677898C (en) | Process for the production of condensation products | |
| DE744281C (en) | Process for the production of imidazoline-N-alkyl- or -oxyalkylsulfonic acids | |
| DE635494C (en) | Process for the preparation of salts of high molecular weight imido ethers, imidothio ethers and amidines | |
| EP0499282A1 (en) | Aqueous concentrate of at least one alkyl- or alkenyl substituted ammonium compound | |
| AT122489B (en) | Process for the preparation of aliphatic-hydroaromatic oxyamines. | |
| AT162920B (en) | Process for the production of nitrogen compounds | |
| CH429763A (en) | Process for the preparation of nonionic, surface-active compounds | |
| DE664309C (en) | Process for the preparation of amides of higher molecular weight carboxylic acids | |
| DE1124938B (en) | Process for the preparation of nonionic polyoxycarboxamides |