Patent GB-943689-A (GB)
Title: Nitrogen compounds
Inventor: BAIRD WILLIAM
IPC: C08G18/32
Filed: 1960-09-08
Abstract: The invention comprises products obtained by reacting polyamines containing at least two amino groups which are primary or secondary amino groups but which do not form part of an oxyaminopropyl group and at least one polyalkyleneoxy chain with polyisocyanates or substances behaving like polyisocyanates.  The products are useful as antistatic agents for treatment of textile fibres.  Suitable polyamines are obtained by reacting an alkylene oxide condensate having at least two hydroxyl groups with thionyl chloride and reacting the product with ammonia or a primary amine. Alternatively the alkylene oxide condensate is reacted with acrylonitrile and the product is converted to an amine by catalytic hydrogenation. Suitable condensates and polyoxyethylene glycols, and ethylene oxide condensates of methylamine, ethylamine, cetylamine, amides, glycerol, sorbitol or pentaerythritol.  The reaction with the polyisocyanate can be effected in benzene, toluene ethylene dichloride, carbon tetrachloride or ethyl acetate.  An isocyanate-bisulphite addition product can be reacted with the amines in aqueous medium.  By carrying out the reaction at low temperature, or with an excess of one reactant or with the polyamine partly neutralized with acetic acid a material soluble or dispersible in water, for subsequent baking on fibres, is obtained.  In examples polyamines derived from polyoxyethylene glycols of M.W. 1,000, 600 and 300 by reaction successively with thionyl chloride and ammonia are reacted in ethanol (in some cases with acetic acid) with a tolylene 2:4 diisocyanate - phenol adduct, or a hexamethylene/diisocyanate/phenol adduct or a hexamethylene sodium bisulphite adduct.  Portions of the products are baked to form films or used to treat textiles.ALSO:Products useful as antistatic agents for treatment of textile fibres are obtained by reacting polyamines containing at least two amino groups which are primary or secondary amino groups but which do not form part of an oxyaminopropyl groups and at least one polyalkylenoxy chain with polyisocyanates or substances behaving like polyisocyanates. Suitable polyamines are obtained by reacting an alkylene oxide condensate having at least two hydroxyl groups with thionyl chloride and reacting the product with ammonia or a primary amine. Alternatively the alkylene oxide condensate is reacted with acrylonitrile and the product is converted to an amine by catalytic hydrogenation.  Suitable condensates are polyoxyethylene glycols, and ethylene oxide condensates of methylamine, ethylamine, cetylamine, amides, glycerol, sorbitol or pentaerythritol.  The reaction with the polyisocyanate can be effected in benzene toluene, ethylene dichloride, carbon tetrachloride or ethyl acetate.  An isocyanate-bisulphite addition product can be reacted with the amines in aqueous medium.  By carrying out the reaction at low temperature, or with an excess of one reactant or with the polyamine partly neutralized with acetic acid a material soluble or dispersible in water, for subsequent baking on fibres, is obtained.  In examples polyamines derived from polyoxyethylene glycols of M.W. 1000, 600 and 300 by reaction successively with thionyl chloride and ammonia are reacted in ethanol (in some cases with acetic acid) with a tolylene 2 : 4 diisocyanate-phenol adduct, or a hexamethylene diisocyanate-phenol adduct, or a hexamethylene/sodium bisulphite adduct.  Portions of the products are baked to form films or used p to treat textiles by impregnation followed by baking.  Fibres which can be treated include those of nylon, polyester and polyacrylonitrile.