Patent GB-464657-A (GB)
Title: Manufacture of amino-carboxylic acids of capillary action
Filed: 1935-09-21
Abstract: Products useful as wetting, washing, and dispersing agents are obtained by reacting a tertiary amine, containing at least one straight chain aliphatic, cycloaliphatic or hydroaromatic radicle of at least nine carbon atoms, with a salt of a halogenated carboxylic acid; such of the products as contain free hydroxyl groups may be sulphonated.  Specified amines are dimethyldodecylamine, diethyloleylamine, methylbenzyldodecylamine, N - methyl - N-dodecylaniline, cycloaliphatic tertiary amines obtainable from abietic acid or naphthenic acids containing at least nine carbon atoms, and tertiary amines obtainable from higher fatty acids or their esters by converting these into nitriles, reducing the nitriles, and alkylating the primary amines so obtained; acids specified in this connection are palm nut acids, palm oil acids, montan acids, linseed oil acids, castor oil acids, hardened fish oil acids, and carboxylic acids obtainable by oxidation of paraffin; amines containing other substituents, e.g. hydroxyl or nitro groups or halogens, may also be used, dioxyethylstearylamine and methyldodecylglucamine being specified.  Specified halogenated carboxylic acids are monochloracetic acid, b -chloropropionic acid, bromosuccinic acid, and 1 : 2 : 5-chloromethylsalicylic acid.  The products may be used in the textile, leather and paper industries, particularly (a) for washing wool, cotton and linen, (b) as dispersing agents in dye baths, (c) for after-soaping prints and improving their fastness to rubbing, (d) as resists or assistants in printing pastes, (e) as additions to bucking lyes and fulling baths and (f) as softening agents for textile goods.  The products may be used alone or mixed with one another or with appropriate additions, in particular (a) other wetting, washing or dispersing agents, such as turkey red oils, sulphuric esters of higher aliphatic alcohols, and sulphonic acids of higher aliphatic or aromatic compounds, such as the reaction products of fatty acids with hydroxyalkyl- or aminoalkyl-sulphonic acids, (b) solvents such as carbon tetrachloride, cyclohexanol, and benzyl alcohol, (c) salts such as sodium sulphate, perborates and water glass, and (d) protective colloids such as glue, gelatin and dextrin.  In the examples, (1) a solution of sodium monochloracetate is added to a tertiary amine mixture (dioxyethyllorolamine) obtained by reducing the nitriles of palm nut oil acids and treating the product with 2 mols. of ethylene oxide per atom of nitrogen; the product obtained by concentrating the reaction mixture may be sulphonated with sulphuric acid monohydrate or chlorsulphonic acid; (2) a solution of sodium monochloracetate is added to a tertiary amine prepared by reducing the nitrile of a hardened fish oil fatty acid and treating the product with ethylene oxide in the presence of caustic soda; (3) dimethyldodecylamine is mixed with a solution of sodium monochloracetate.  Specification 442,767 is referred to.ALSO:Products useful as wetting, washing, and dispersing agents are obtained by reacting a tertiary amine, containing at least one straightchain aliphatic, cycloaliphatic or hydroaromatic radicle of at least nine carbon atoms, with a salt of a halogenated carboxylic acid; such of the products as contain free hydroxyl groups may be sulphonated.  Specified amines are dimethyldodecylamine, diethyloleylamine, methylbenzyl dodecylamine, N - methyl - N - dodecylaniline, cycloaliphatic tertiary amines obtainable from abietic acid or naphthenic acids containing at least nine carbon atoms, and tertiary amines obtainable from higher fatty acids or their esters, such as palm nut acids, palm oil acids, montan acids, linseed oil acids, castor oil acids, hardened fish oil acids, and carboxylic acids obtainable by oxidation of paraffin; amines containing other substituents, e.g. hydroxyl or nitro groups or halogens, may also be used, dioxyethylstearylamine and methyldodecylglucamine being specified.  Specified halogenated carboxylic acids are monochloracetic acid, b -chloropropionic acid, bromosuccinic acid, and 1 : 2 : 5-chloromethylsalicylic acid.  The products may be used in the textile, leather and paper industries, particularly for washing wool, cotton and linen and as diapersing agents in dye baths.  They may be used alone or mixed with one another or with appropriate additions, in particular (a) other wetting, washing or dispersing agents, such as turkey red oils, sulphuric esters of higher aliphatic alcohols, and sulphonic acids of higher aliphatic or aromatic compounds, such as the reaction products of fatty acids with hydroxyalkyl- or aminoalkyl-sulphonic acids, (b) solvents such as carbon tetrachloride, cyclohexanol, and benzyl alcohol, (c) salts such as sodium sulphate, perborates and water glass, and (d) protective colloids such as glue, gelatin and dextrin. In the examples: (1) a solution of sodium mono-chloracetate is added to a tertiary amine mixture ("dioxyethyllorolamine") obtained by reducing the nitriles of palm nut oil acids and treating the product with 2 mols. of ethylene oxide per atom of nitrogen; the product obtained by concentrating the reaction mixture may be sulphonated with sulphuric acid monohydrate or chlorsulphonic acid; (2) a solution of sodium monochloracetate is added to a tertiary amine prepared by reducing the nitrile of a hardened fish oil fatty acid and treating the product with ethylene oxide in the presence of caustic soda; (3) dimethyldodecylamine is mixed with a solution of sodium monochloracetate.  Specification 442,767 is referred to.