Patent GB-414712-A (GB)
Title: Improvements in the manufacture and production of substances suitable as wetting, washing, dispersing and like agents
Filed: 1932-11-05
Abstract: Products stated to be useful as dispersing agents are obtained by causing monomeric aliphatic aldehydes or ketones containing more than six carbon atoms to react with the amino groups of primary or secondary amines and making the resulting condensation products soluble by converting them into the corresponding ammonium salts or quaternary ammonium salts after saturating with hydrogen the double bond of the imino compounds which are produced when primary amines are used.  Alternatively amines may be used which contain groups which render the products soluble in water namely, quaternary ammonium, ammonium, hydroxyalkylenepolyether, sulphonic, sulphuric or phosphoric groups.  Further, if the primary condensation products contain halogen or mineral acid ester groups they may be made soluble by treating with sulphites, or if they contain hydroxy groups or hydrogen attached to nitrogen they may be treated with alkyleneoxides, or if they contain hydroxy groups they may be treated with sulphuric or phosphoric acid.  In an example lauric aldehyde is condensed with sulphanilic acid sodium salt; the product has wetting and emulsifying power.  The following aldehydes and ketones are specified: stearic, oleic, ricinoleic, caprylic, caprinic, myristic, palmitic, 2-ethylcapronic, undecylenic, and nonylic aldehydes, heptadecylmethylketone, heptadecylethylketone, heptadecylpropylketone, diheptadecylketone, heptadecenylethylketone, heptadecenylmethylketone, nonylmethylketone, undecylmethylketone, decenylethylketone, pentadecylmethylketone and laurone.  The mixtures of aldehydes or ketones corresponding to the fatty acids are particularly suitable.  Coconut, soyabean, rapeseed, cotton, linseed, train oil and montanic acids are mentioned.  Mono and triethanolanimes may be used.  Specifications 343,098, 343,901, 348,040, 360,539; 364,000, [Group IV]; 375,770, 377,678, 380,431, and 414,772 are referred to.ALSO:Products stated to be useful as wetting, washing, foaming and dispersing agents are obtained by causing monomeric aliphatic aldehydes or ketones containing more than six carbon atoms to react with the amino groups of primary or secondary amines and making the resulting condensation products soluble by converting them into the corresponding ammonium salts or quaternary ammonium salts after saturating with hydrogen the double bond of the imino compounds which are produced when primary amines are used. Alternatively, amines may be used which contain groups which render the products soluble in water, namely quaternary ammonium, ammonium, hydroxyalkylenepolyether, sulphonic, sulphuric or phosphoric groups. Further, if the primary condensation products contain halogen or mineral acid ester groups, they may be made soluble by treating with sulphites, or if they contain hydroxy groups or hydrogen attached to nitrogen they may be treated with alkyleneoxides, or if they contain hydroxy groups they may be treated with sulphuric or phosphoric acid. In examples, (1) lauric aldehyde is condensed with ethylenediamine in the presence of cobalt as catalyst and after treatment with hydrogen the product is converted into its hydrochloric acid salt; it may be used for fixing substantive dyestuffs on cotton or viscose; by treatment with ethylene oxide it is rendered more soluble; (2) lauric aldehyde is condensed with sulphanilic acid sodium salt; the product has wetting and emulsifying power; (3) heptadecenylmethylketone, obtained by removing carbondioxide and water by heating a mixture of oleic and acetic acids with manganese as catalyst, is condensed with 1-dimethylamino-3-aminopropane which may be obtained by treating acrylic nitrile with dimethylamine and reducing the product.  By addition of hydrochloric acid a soluble wetting and foaming agent is obtained; (4) the primary condensation product of example 1 is rendered soluble by treatment with ethylbromide; (5) lauric aldehyde is heated with diethanolamine in the presence of acetic and formic acids, and the product esterified with chlorsulphonic acid.  The following aldehydes and ketones are specified: stearic, oleic, ricinoleic, caprylic, caprinic, myristic, palmitic, 2-ethylcapronic, undecylenic, and nonylic aldehydes, heptadecylmethylketone, heptadecylethylketone, heptadecylpropylketone, diheptadecylketone, heptadecenylethylketone, heptadecenylmethylketone, nonylmethylketone, undecylmethylketone, decenylethylketone, pentadecylmethylketone and laurone.  The mixtures of aldehydes or ketones corresponding to the fatty acids are particularly suitable.  Coco nut, soya bean, rapeseed, cotton, linseed, train oil and montanic acids are mentioned.  Mono and triethanolamines may be used.  Specifications 343,098, 343,901, 348,040, 360,539, 364,000, 375,770, 377,678, 380,431, and 414,772 are referred to.  The higher aldehydes used as starting materials are obtained by catalytic dehydrogenation of the corresponding alcohols, and the higher ketones are obtained by splitting off carbon dioxide and water from the corresponding fatty acids.