CH200669A - Process for the preparation of a quaternary nitrogen compound. - Google Patents

Description

       

  Process for the preparation of a quaternary nitrogen compound. It has been found that a number of valuable, new compounds are obtained if aromatic amines, which contain a higher molecular weight, saturated or unsaturated aliphatic radical with more than eight carbon atoms on the nitrogen atom, with the usual,

       converted into the quaternary ammonium compounds using low molecular weight alkylating agents. Reactive esters of aliphatic, low molecular weight alcohols such as dialkyl sulfates, alkyl halides, etc. are particularly suitable for this purpose.



  The new quaternary compounds can be used for a wide variety of purposes. They form valuable wetting, dispersing and emulsifying agents or agents to improve water fastness, in particular softeners for native and unprecipitated cellulose, stripping agents for Naphtol-AS dyeings, etc.

   Some of them are also suitable for protecting wool, feathers, furs, hair, leather and the like from moths and other pests. Some of the new compounds also have pronounced bactericidal and fungicidal properties.



  Similar quaternary compounds have already become known, on the one hand a higher molecular weight, aliphatic, optionally substituted and / or interrupted by other atoms, but not acy lated hydrocarbon radical, on the other hand at least one aliphatically bound organic radical containing one or more double bonds contained in nitrogen.

   For their structure, it is stated that the usual methods lead to the goal, in particular that this is achieved by the action of suitable esters, which contain the particular higher molecular weight radical, on tertiary amines, the aliphatically bonded radical containing double bonds on nitrogen are substituted, can happen.



  If you apply this method to tertiary, aromatic amines, z. B. on diethyl aniline, by letting the bromide of technical dodecyl alcohol act on it, no conversion to the quaternary compound takes place. From this one would have to draw the conclusion that quaternary ammonium compounds that contain a higher molecular weight and a directly bound aromatic radical cannot be represented.

   All the more surprising is the fact that a different, specific sequence of alkylation leads to the goal, namely that aromatic amines which are substituted on the nitrogen by a higher molecular weight alkyl radical are easily and quantitatively converted into the corresponding quaternary compounds by conventional alkylation can be transferred.



  The subject of the present patent is a process for the production of a quaternary nitrogen compound, characterized in that dodecylaniline is exhaustively methylated with dimethyl sulfate. The new quaternary ammonium compound, dodecyl dimethylaniline methyl sulfate, a waxy, light yellow paste, is clearly soluble in water;

   it 'can be used as a wetting, dispersing and emulsifying agent, as a plasticizer for native and reprecipitated cellulose, as an agent to improve the waterfastness of direct dyeings and as a stripping agent for Naphtol-AS dyeings. The compound is also suitable for protecting feathers, fur, hair and other fibrous materials from caterpillars and other pests.

   It also has pronounced bactericidal and fungicidal properties.



       Example: 52 parts of dodecylaniline, prepared by the usual process, are dissolved in 200 parts by volume of chlorobenzene and 25.5 parts of calc. Soda added.

       At <B> 100 '</B>, 30 parts of dimethyl sulfate are added dropwise and the mixture is stirred for 12 hours. The insoluble inorganic salts are then filtered off, a further 30 parts of dimethyl sulfate are added and the mixture is stirred at 90 to 95 for a further 8 hours. Then the chlorobenzene is blown off with steam and the remaining clear, aqueous solution is evaporated to dryness.

   The new quaternary compound, dodecyl dimethylaniline methyl sulfate, is obtained as a waxy, light yellow paste that is clearly soluble in water.


    

Claims (1)

PATENT CLAIM: Process for the production of a quaternary nitrogen compound, characterized in that dodecylaniline is exhaustively methylated with dimethyl sulfate. The new quaternary ammonium compound, dodecyl dimethylaniline methyl sulfate, a waxy, light yellow paste, is clearly soluble in water; it can be used as a wetting, dispersing and emulsifying agent, as a plasticizer for native and reprecipitated cellulose, as an agent to improve the water resistance of direct dyeings and as a stripping agent for Naphtol-AS dyeing agents. The connection is also suitable for protecting animals and fur. Hair and other fibrous materials from caterpillars and other pests. It also has pronounced bactericidal and fungicidal properties.