Patent GB-455379-A (GB)
Title: Manufacture and application of substances having capillary activity
IPC: D06L1/12
Filed: 1935-01-15
Abstract: Compounds of the formula ARX, where A is an aryl radicle, R is an aliphatic hydrocarbon radicle linked to A by a C--C linkage, and X is a carboxylic, sulphonic, substituted amino, or quaternary ammonium group, are treated in the presence of an acid condensing agent with at least two molecular proportions of an aliphatic alcohol containing at least three carbon atoms, or of an olefine or hydrohalic ester obtainable therefrom, until there is obtained a product which, in the form of an alkali-metal salt (when X is a carboxylic or sulphonic group), or in the form of a mineral or organic acid salt (when X is a substituted amino or a quaternary ammonium group), dissolves in water to give a clear and strongly frothing solution.  The products are of the type R<1>nARX, where R<1> is an aliphatic radicle of at least three carbon atoms and n is two or a higher whole number.  When X is a carboxylic group the products may be condensed, in the form of their chlorides, with an oxyalkylsulphonic acid, an aminoalkylsulphonic acid, or a sulphuric ester of an alkylolamine. All the products obtainable as described above, and also compounds of the second formula above in which X is a free amino group, are useful as wetting, washing and emulsifying agents and may be applied in washing white goods or piece goods, washing loose wool, and kier-boiling, or added to dye baths or carbonizing baths; the compounds may be used alone or mixed with other substances such as soaps, salts, solvents and emulsion stabilizers.  In the examples: (1) phenylacetic acid and n-butyl alcohol, heated in the presence of sulphuric acid, yield triisobutylphenylacetic acid and a smaller amount of diisobutylphenylacetic acid; the product (as sodium salt) is useful as a washing agent; isohexyl alcohol may be used in place of butyl alcohol; (2) hydrocinnamic acid and n-butyl alcohol, treated as in example 1, yield tri- or tetra-isobutylhydrocinnamic acid; (3) a -naphthylacetic acid and n-butyl alcohol are condensed as in example 1; (4) d -phenyl-n-valeric acid (obtained by condensing cinnamic aldehyde with malonic acid, and hydrogenating and decarboxylating the product) is condensed with n-butyl alcohol as in example 1; (5) phenylacetic acid is condensed with n-dodecylene in the presence of boron trifluoride; (6) an aqueous solution of sodium tetrabutylphenylacetate, obtained from phenylacetic acid and butyl alcohol as in example 1, is used for washing white linen goods; (7) experiments illustrating the use of the product of example 3 as a hot wetting agent are described; (8) an aqueous solution of sodium carbonate and the sodium salt of the product of example 4 is used for washing white linen goods; (9) triisobutylphenylacetyl chloride is condensed with sodium oxyethanesulphonate to yield a product useful for wetting and cleansing wool and cotton; (10) triisobutylphenylacetyl chloride is condensed with the sodium salt of methyltaurine to yield a product useful for washing goods soiled with oil; (11) a product useful as a levelling agent in dyeing with vat dyes is obtained by the action of 22 mols. of ethylene oxide on triisobutylphenylethylamine, which is itself obtained by converting triisobutyl phenylacetic acid into its nitrile by reaction with ammonia at above 300 DEG  C., followed by hydrogenation of the nitrile; (12) a product for use as a washing agent is prepared by treating triisobutylphenylethylamine with monochloracetic acid in an alkaline medium; (13) benzylsulphonic acid (from benzyl chloride and sodium sulphite) is treated with propyl alcohol in the presence of sulphuric acid to yield a mixture of tri- and tetra-propylbenzylsulphonic acid, useful as a wetting agent; (14) phenylacetic acid and n-butyl (or propyl) alcohol are condensed in the presence of boron trifluoride to yield a polybutyl- (or polypropyl-) phenylacetic acid; (15) phenylacetic acid and isoheptylene are condensed in the presence of boron trifluoride; (16) a composition for washing linen comprises the sodium salt of the product of example 2, soda, sodium perborate, sodium pyrophosphate, and waterglass; (17) the chloride of the polyisobutylhydrocinnamic acid obtained in example 2 is condensed with the potassium salt of methyltaurine to yield a product useful for washing goods soiled with oil; (18) a product useful as a liquid soap is prepared by converting triisobutylphenylethylamine into a quaternary ammonium compound by reaction with dimethyl sulphate; (19) a product useful as a washing agent is prepared by condensing triisobutylphenylethylamine successively with monochloracetic acid and methyl chloride in an alkaline medium; the product may be converted into a betaine derivative by further reaction with methyl chloride; it may be used alone or with soda; (20) the chloride of diisohexylhydrocinnamic acid is condensed in an alkaline medium with sodium aminoethanol sulphate to yield a product useful for washing wool; (21) an aqueous solution of a sodium polydodecylphenylacetate, obtained as in example 5, is used for washing linen; (22) the acetate of triisobutylphenylethylamine is used as a wetting agent; (23) triethylbenzylammonium chloride is condensed with n-butylalcohol in the presence of sulphuric acid.  Other products specified are polyisohexyl- and diisopropyl-naphthylacetic acid.  Other specified starting materials are ethylphenylacetic acid, a -phenylbutyric acid, and acenaphthenylacetic acid.  Other specified alkylating agents are hexyl, lauryl, stearyl and isobutyl alcohols and the corresponding olefines and hydrohalic esters, and also monobutyl glycol.  Other specified alkyl radicles which may be introduced are chlorohexyl and oxybutyl.  Other specified condensing agents are oleum, phosphoric acid, and aluminium chloride.  The Provisional Specification indicates that X in the formul  above may be a hydroxy, sulphuric ester, free amino, polyglycol or polyglycerol group, and that R<1> in the second formula may be an ethyl group; tetrahydronaphthylacetic acid, phenylethyl alcohol, phenylethylamine and monobenzyltriglycol ether are additional specified starting materials; diisopropyltetrahydronaphthylacetic acid is an additional specified product.ALSO:Compounds of the formula ARX, where A is an aryl radicle, R is an aliphatic hydrocarbon radicle linked to A by a C--C linkage, and X is a carboxylic, sulphonic, substituted amino, or quaternary ammonium group, are treated in the presence of an acid condensing agent with at least two molecular proportions of an aliphatic alcohol containing at least three carbon atoms, or of an olefine or hydrohalic ester obtainable therefrom, until there is obtained a product which, in the form of an alkali-metal salt (when X is a carboxylic or sulphonic group), or in the form of a mineral or organic acid salt (when X is a substituted amino or a quaternary ammonium group), dissolves in water to give a clear and strongly frothing solution.  The products are of the type R<1>nARX, where R<1> is an aliphatic radicle of at least three carbon atoms and n is two or a higher whole number.  When X is a carboxylic group the products may be condensed, in the form of their chlorides, with an oxyalkylsulphonic acid, an aminoalkylsulphonic acid, or a sulphuric ester of an alkylolamine.  All the products obtainable as described above, and also compounds of the second formula above in which X is a free amino group, are useful as washing and emulsifying agents; they may be used alone or mixed with other substances such as soaps, salts, solvents and emulsion stabilizers.  In the examples: (1) phenylacetic acid and n-butyl alcohol yield di- and tri-isobutylphenylacetic acid; the product (as sodium salt) is useful as a washing agent; isohexyl alcohol may be used in place of butyl alcohol; (2) hydrocinnamic acid and n-butyl alcohol yield tri- or tetra-isobutylhydrocinnamic acid; (3) a -naphthylacetic acid is condensed with n-butyl alcohol; (4) d -phenyl-n-valeric acid is condensed with n-butyl alcohol; (5) phenylacetic acid is condensed with n-dodecylene; (6) an aqueous solution of sodium tetrabutylphenylacetate is used for washing white linen goods; (7) an aqueous solution of sodium carbonate and the sodium salt of the product of example 4 is used for washing white linen goods; (8) triisobutylphenylacetyl chloride is condensed with sodium oxyethanesulphonate to yield a product useful for cleansing wool and cotton; (9) triisobutylphenylacetyl chloride is condensed with the sodium salt of methyltaurine to yield a product useful for washing goods soiled with oil; (10) a product for use as a washing agent is prepared by treating triisobutylphenylethylamine with monochloracetic acid; (11) benzylsulphonic acid is treated with propyl alcohol to yield a mixture of tri- and tetrapropylbenzylsulphonic acid; (12) phenylacetic acid and n-butyl (or propyl) alcohol are condensed to yield a polybutyl-(or polypropyl-) phenylacetic acid; (13) phenylacetic acid and isoheptylene are condensed in the presence of boron trifluoride; (14) a composition for washing linen comprises the sodium salt of the product of example 2 soda, sodium perborate, sodium pyrophosphate, and waterglass; (15) the chloride of the polyisobutylhydrocinnamic acid obtained in example 2 is condensed with the potassium salt of methyltaurine to yield a product useful for washing goods soiled with oil; (16) a product useful as a liquid soap is prepared by converting triisobutylphenyethylamine into a quaternary ammonium compound by reaction with dimethyl sulphate; (17) a product useful as a washing agent is prepared by condensing triisobutylphenylethylamine successively with monochloracetic acid and methyl chloride in an alkaline medium; the product may be converted into a betaine derivative by further reaction with methyl chloride; it may be used alone or with soda; (18) the chloride of diisohexylhydrocinnamic acid is condensed with sodium aminoethanol