Patent GB-388876-A (GB)
Title: Improvements in the manufacture and production of assistants for the textile and related industries
IPC: C07C255/26
Filed: 1931-11-28
Abstract: Assistants for the textile and related industries, of the probable general formula <FORM:0388876/IV/1> where R is an aliphatic radicle containing at least three carbon atoms, X is hydrogen or an aliphatic radicle and Y is hydrogen or a radicle of a base such as sodium or potassium, are manufactured by reacting N - b -hydroxyalkylaminocarboxylic acids containing a hydrogen atom connected to the nitrogen atom with halides of aliphatic carboxylic acids containing at least four carbon atoms. The said halides may be halides of open chain aliphatic or cycloaliphatic carboxylic acids, especially those of fatty acids of natural origin and particularly of animal and vegetable origin, e.g. butyric, lauric, palmitic, stearic, oleic, montanic and myristic acids, halides of mixtures of such acids, e.g. the acids of coconut or pea-nut oils or train oils, halides of the acids produced by the oxidation of paraffin wax and naphthenic acids, and halides of halogenated acids, e.g. the chlorides of dichlorostearic and monochloropalmitic acids (obtainable by chlorinating stearic and palmitic acid chlorides respectively). The N-b -hydroxyalkylaminocarboxylic acids are obtainable by saponifying the nitriles obtainable according to Specification 388,874.  The condensation is preferably carried out in the presence of sufficient alkali to neutralize the halogen hydride, the alkali, such as sodium or potassium hydroxide or carbonate or calcium hydroxide, being usually employed as an aqueous solution. Alternatively the acid halide is introduced into an aqueous solution of the alkali metal salts of the aminocarboxylic acids. The alkali halides formed as bye-products may be left in the reaction products without impairing their properties or may be removed.  The reaction is preferably carried out at 0-80 DEG  C.  The products are suitable as wetting, washing, dispersing and softening agents in the textile and like industries, and may be employed in acid, alkaline or neutral baths without deposits of difficulty soluble salts even when using water containing lime. They are particularly useful in the parchmentizing or mercerizing treatment of cotton fabrics or paper with concentrated sulphuric acid, most of them, particularly those from acid halides containing 8-14 carbon atoms, dissolving easily in the sulphuric acid employed in parchmentizing paper, the addition of 0,5-10 per cent by weight of the substances causing rapid and uniform wetting so that previous wetting is unnecessary.  They may also be added to baths for rendering artificial silk smooth and soft, and may be employed as dispersing agents for dyestuffs, resins, waxes, paraffin oils or waxes, mineral or vegetable oils or fats and organic solvents.  They may be used alone or with other substances, such as soaps, Turkey red oils or dispersive sulphuric esters of other aliphatic compounds or sulphonic acids of aromatic compounds, or with salts such as perborates, Glauber's salt or tartaric acid salts, or with glue, gum arabic or dextrine, for instance N-hydroxyethylglycollstearic amide may be mixed with the sulphuric ester of monoethanolamine coco fatty acid amide.  The compounds may also be employed in conjunction with organic solvents, such as cyclohexanol, tetrahydronapthalene, water-insoluble liquid or solid alcohols or ketones.  In examples: (1) hydroxyethylaminoacetonitrile (obtainable from monoethanolamine, formaldehyde and hydrocyanic acid) is saponified with caustic soda and the product condensed with coconut oil acid chloride; the product has good wetting power and may be dissolved in alkalies or strong mineral acids, e.g. sulphuric acid; the coconut oil acid chloride may be replaced by stearic chloride; the product, together with oleylmonoethanolamide sulphuric ester or the amide obtainable by condensing coconut oil fatty acid chloride with aminoethanol sulphuric ester according to Specification 386,966, may be added to a bath for rendering artificial silk smooth and soft; (2) a -n-propyl-N-hydroxyethylaminoacetonitrile (obtainable from monoethanolamine, n-butyraldehyde and hydrocyanic acid) is saponified with caustic soda and the product condensed with n-butyryl chloride; the product has good wetting power in neutral or alkaline baths, e.g. caustic mercerizing lyes, or in sulphuric acid; the free acid may be liberated by the action of acids, e.g. hydrochloric or sulphuric acid; (3) the acid obtainable by saponifying the nitrile obtained from monoethanolamine, methylisopropyl ketone and hydrocyanic acid is condensed with stearic chloride; the paste is dried on the water bath yielding a powder which is an excellent washing agent; (4) N-b -hydroxypropylaminoacetonitrile (obtainable from b -hydroxy-n-propylamine, formaldehyde and hydrocyanic acid) is saponified with caustic soda and the product condensed with d-campholic acid chloride (1 : 2 : 2 : 3 - tetramethylcyclopentane - 1 - carboxylic acid chloride); the product when added to sulphuric acid increases its wetting power towards textiles; (5) the sodium salt of hydroxyethylaminoacetic acid (obtainable by saponifying the corresponding nitrile with caustic soda) is condensed with the chloride obtained by treating naphthenic acids with phosphorus trichloride; the product may be used as a softening agent for artificial silk from viscose.ALSO:Compounds of the general formula: <FORM:0388876/III/1> where R is an aliphatic radicle containing at least three carbon atoms, X is hydrogen or an aliphatic radicle and Y is hydrogen or a radicle of a base such as sodium or potassium, may be employed as dispersing-agents for dyestuffs, resins, waxes, paraffin oils or waxes, mineral or vegetable oils or fats and organic solvents, or as washing agents, alone or in admixture with other substances, such as soaps, Turkey red oils or dispersive sulphuric esters of other aliphatic compounds or sulphonic acids of aromatic compounds, or with salts such as perborates, Glauber's salt or tartaric acid salts, or with glue, gum arabic or dextrine, or in conjunction with organic solvents, such as cyclohexanol, tetrahydronaphthalene, water-insoluble liquid or solid alcohols or ketones.  Specifications 386,966; and 388,874, [Group IV], are referred to.