Patent GB-446737-A (GB)
Title: Manufacture of amino-carboxylic acids of capillary action
Filed: 1934-08-21
Abstract: Products useful as wetting, washing, and dispersing agents are obtained by reacting alkyl halides or other alkylating agents or other halogenated compounds with secondary or tertiary aminocarboxylic acids containing a straight-chain aliphatic, cycloaliphatic or hydroaromatic radicle of at least nine carbon atoms, but not containing a hydroxyalkyl group.  Specified aminocarboxylic acids are: (a) dodecylaminoacetic acid, octadecylaminoacetic acid, octadecenylaminoacetic acid, dodecylmethylaminoacetic acid, hexadecyliminodiacetic acid, a -dimethylaminomyristic acid, 10-dimethylaminostearic acid, octadecyliminodiacetic acid, and a -diethylaminostearic acid; (b) non-hydroxylated aminocarboxylic acids obtainable from abietic and naphthenic acids, or from higher fatty acids or their esters, e.g. palm-nut oil 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, for example by converting the acids into nitriles, hydrogenating the nitriles to yield amines, and condensing the latter with halogencarboxylic acids; (c) the reaction products of higher alcohols, aldehydes or ketones, e.g. the neutral oxidation products of paraffin, with ammonia and halogencarboxylic acids. Specified alkylating agents and halogenated compounds are monochloracetic acid, b -chloropropionic acid, bromosuccinic acid, 1 : 2 : 5-chloromethylsalicylic acid, methyl chloride, ethyl chloride, chlorethanesulphonic acid, benzyl chloride and its sulphonic acids, bromobenzene, alkylene oxides such as ethylene or propylene oxide, dimethyl sulphate, and sodium butyl sulphate. The products may be applied in 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 mercerization and bucking lyes; (f) for fulling; and (g) 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 water glass; and (d) protective colloids such as glue, gelatin and dextrin.  In the examples: (1) sodium dodecylaminoacetate and sodium chloracetate yield sodium dodecyliminodiacetate; an aqueous solution of the product, with or without sodium carbonate, is useful for washing linen; (2) sodium dodecylaminoacetate and ethylene oxide yield sodium oxyethyldodecyl aminoacetate; (3) an amine mixture ("lorolamine") obtained from palm-nut oil fatty acid, is treated with chloracetic acid in an alkaline medium; the sodium monolorolaminoacetate first formed reacts further with the sodium chloracetate, and yields a product containing sodium loroliminodiacetate and the corresponding betaine; (4) octadecylamine and sodium monochloracetate yield sodium octadecylaminoacetate, which is then treated with dimethyl sulphate; oleylamine may be used in place of octadecylamine; (5) an amine obtained from hardened fish oil fatty acid (by way of the nitrile and reduction) is condensed with sodium monochloracetate, and the secondary aminoacetate so obtained is treated with methyl chloride; (6) an amine obtained from a technical naphthenic acid, containing constituents of eight, nine and more carbon atoms, is treated with potassium monochloracetate, and the product is treated with dimethyl sulphate; (7) an amine obtained from abietic acid (by way of the nitrile and reduction) is treated with sodium monochloracetate, and the product is treated with dimethyl sulphate; (8) an amine obtained from hardened fish oil acid (by way of the nitrile and reduction) is treated with sodium b -chloropropionate, and the product is treated with methyl chloride; (9) sodium octadecyliminodiacetate is treated with dimethyl sulphate; (10) the amine used in example 8 is treated with sodium monochloracetate or (example 11) sodium b -chloropropionate, and the product is treated with dimethyl sulphate; (12) a -bromostearic acid is treated with diethylamine, and the product is treated with dimethyl sulphate; the final product is believed to be of a betaine character; (13) as in example 9, but under somewhat different conditions; the product is useful as a levelling agent in vat-dyeing; (14) an amine of the type used in example 8 is condensed with two molecules of chloracetic acid, and the product is treated with dimethyl sulphate; the final product is useful as a levelling and through-dyeing agent in dyeing with vat dyes or in an acid bath. Specification 416,631 is referred to.  The Provisional Specification describes generally the alkylation, arylation or aralkylation of primary or secondary amino compounds containing at least one aliphatic radicle of at least six carbon atoms, or a cycloaliphatic or hydroaromatic radicle, the reagents being so selected that the products contain one or more carboxylic groups.  Specified amino compounds are dodecylamine; methyldodecylamine; hexyloctylamine; dihexylamine; amine mixtures obtainable from higher fatty acids, or their esters, such as palm nut fatty acids, montanic acids, and the acids obtained by the oxidation of paraffin; reaction products of ammonia or primary amines with higher alcohols, aldehydes and ketones, such as the neutral oxidation products of paraffin; decahydronaphthylamine; amines corresponding to abietic acid and naphthenic acids; alkylaryl amines such as N-dodecyl- or C-dodecylaniline; halogen- and nitro-amines; hydroxy-amines such as hydroxyethyloleylamine, dihydroxypropyldodecylamine, glucamine, methylglucamine, dodecylglucamine, and octadecylglucamine; a  - aminolauric and a -aminostearic acids.  Amino compounds not containing a carboxylic group may be reacted with halogenated carboxylic acids such as monochloracetic acid, b -chloropropionic acid, and bromosuccinic acid.  Primary amino compounds containing a carboxylic group may be treated as described in the complete Specification.  The products are useful as described above.  The Specification includes the examples given in Specification 446,813 and also an example in which dodecylamine and monochloracetic acid are reacted in an alkaline medium.  The manufacture of methyldodecylaminoacetic acid from methyldodecylamine and chloracetic acid is mentioned.ALSO:Products useful as dispersing agents are obtained by reacting alkyl halides or other alkylating agents or other halogenated compounds with secondary or tertiary aminocarboxylic acids containing a straight-chain aliphatic, cycloaliphatic or hydroaromatic radicle of at least nine carbon atoms, but not containing a hydroxyalkyl group.  Specified aminocarboxylic acids are (a) dodecylaminoacetic acid, octadecenylaminoacetic acid, octadecenylmethylaminoacetic acid, dodecylmethylaminoacetic hexadecyliminodiacetic acid, a -dimethylamino myristic acid, 10-dimethylaminostearic acid, octadecyl-imino diacetic acid, and a -diethylaminostearic acid; (b) non-hydroxylated aminocarboxylic acids obtainable from abietic and naphthenic acids, or from higher fatty acids or their esters, e.g. palm-nut oil 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, for example by converting the acids into nitriles, hydrogenating the nitriles to yield amines, and condensing the latter with halogencarboxylic acids; (c) the reaction products of higher alcohols, aldehydes or ketones, e.g. the neutral oxidation products of paraffin, with ammonia and halogencarboxylic acids.  Specified alkylating agents and halogenated compounds are monochloracetic acid, b -chloropropionic acid, bromosuccinic acid, 1 : 2 : 5-chloromethylsalicylic acid, methyl chloride, ethyl chloride, chlorethane sulphonic acid, benzyl chloride and its sulphonic acids, bromobenzene, alkylene oxides such as ethylene or propylene oxide, dimethyl sulphate, and sodium butyl sulphate.  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 water glass; and (d) protective colloids such as glue, gelatin and dextrin.  In the examples: (1) sodium dodecylaminoacetate and sodium chloracetate yield sodium dodecyliminodiacetate; an aqueous solution of the product, with or without sodium carbonate, is useful for washing linen; (2) sodium dodecylaminoacetate and ethylene oxide yield sodium oxyethyldodecylaminoacetate; (3) an amine mixture (lorolamine) obtained from palm-nut oil fatty acid, is treated with chloracetic acid in an alkaline medium; the sodium monolorolaminoacetate first formed reacts further with the sodium chloracetate, and yields a product containing sodium loroliminodiacetate and the corresponding betaine; (4) octadecylamine and sodium monochloracetate yield sodium octadecylamino acetate, which is then treated with dimethyl sulphate; oleylamine may be used in place of octadecylamine; (5) an amine obtained from hardened fish oil fatty acid (by way of the nitrile and reduction) is condensed with sodium monochloracetate, and the secondary aminoacetate so obtained is treated with