Patent GB-446813-A (GB)
Title: Manufacture of amino-carboxylic acids of capillary action
IPC: D06M13/342
Filed: 1934-08-21
Abstract: Products useful as wetting, washing, and dispersing agents are obtained by reacting non-hydroxylated secondary amines containing a straight-chain aliphatic, cycloaliphatic or hydroaromatic radicle of at least nine carbon atoms with a salt of a p  halogencarboxylic acid.  Specified amines are (a) methyldodecylamine, methyloleylamine and N-dodecylaniline; (b) non-hydroxylated secondary amines obtainable, for example, by the process of Specification 421,718, from higher fatty acids or their esters, such as palm nut fatty acid, palm oil fatty acid, montanic acid, acids obtained by the oxidation of paraffin, linseed oil fatty acid, castor oil fatty acid, and hardened fish oil fatty acid; (c) the reaction products of primary amines with higher alcohols, ketones or aldehydes, e.g. the neutral oxidation products of paraffin; (d) cycloaliphatic secondary amines such as those derivable from abietic acids or naphthenic acids containing at least nine carbon atoms.  Specified halogencarboxylic acids are monochloracetic, b -chloropropionic, bromosuccinic, and 1 : 2 : 5-chloromethylsalicylic acids.  The products may be applied in the textile, leather and paper industries, particularly (a) in washing wool, cotton and linen; (b) as assistants or dispersing or levelling agents in dye baths; (c) for after-soaping prints and improving their fastness to rubbing; (d) as assistants or resists in printing pastes; (e) in fulling baths and bucking lyes; and (f) as softening agents for textiles.  The products may be used alone or with appropriate additions such as (a) other wetting, washing or dispersing agents such as turkey red oil, sulphuric esters of higher 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 waterglass; and (d) protective colloids such as glue, gelatin and dextrin.  In the examples: (1) methyldodecylamine and sodium monochloracetate in aqueous solution yield methyldodecylaminoacetic acid, the sodium salt of which is useful as a softening agent for artificial silk; (2) methyloleylamine and sodium monochloracetate similarly yield methyloleylaminoacetic acid, the sodium salt of which is useful as a wetting agent.  A sample has been furnished under Sect. 2 (5) of methyldodecylaminoacetic acid prepared by heating an alcoholic solution of methyldodecylamine with dry sodium monochloracetate.  The Provisional Specification includes additional matter, included also in Specification 446,737.ALSO:Products useful as dispersing agents are obtained by reacting non-hydroxylated secondary amines containing a straight-chain aliphatic, cycloaliphatic or hydroaromatic radicle of at least nine carbon atoms with a salt of a halogencarboxylic acid. Specified amines are (a) methyldodecylamine, methyloleylamine and N-dodecylaniline; 9b) non-hydroxylated secondary amines obtainable, for example by the process of Specification 421,718, from higher fatty acids or their esters, such as palm nut fatty acid, palm oil fatty acid, montanic acid, acids obtained by the oxidation of paraffin, linseed oil fatty acid, castor oil fatty acid, and hardened fish oil fatty acid; (c) the reaction products of primary amines with higher alcohols, ketones or aldehydes, e.g. the neutral oxidation products of paraffin; (d) cycloaliphatic secondary amines such as those derivable from abietic acids or naphthenic acids containing at least nine carbon atoms.  Specified halogencarboxylic acids are monochloracetic, b -chloropropionic, bromosuccinic, and 1 : 2 : 5-chloromethylsalicylic acids.  The products may be used alone or with appropriate additions such as (a) other wetting, washing, or dispersing agents such as turkey red oil, sulphuric esters of higher alcohols, and sulphonic acids of higher aliphatic or aromatic compounds, such as the reaction products of fatty acids with hydroxyalkyl- or amino-alkyl-sulphonic acids; (b) solvents such as carbon tetrachloride, cyclohexanol and benzyl alcohol; (c) salts such as sodium sulphate, perborates and waterglass; and (d) protective colloids such as glue-gelatin and dextrin.  In the examples: (1) methyldodecylamine and sodium monochloracetate in aqueous solution yield methyldodecylaminoacetic acid; (2) methyloleylamine and sodium monochloracetate similarly yield methyloleylaminoacetic acid.  A sample has been filed under Sect. 2 (5) of methyldodecylaminoacetic acid.  the Provisional Specification includes additional matter, included also in Specification 446,737.