Patent GB-751244-A (GB)
Title: Process for the preparation of wetting agents
IPC: C08G65/28
Filed: 1954-03-03
Abstract: The invention comprises compounds of the general formula R-O-CH2-CHOH-CH2-SO3M wherein R stands for an alkyl radical containing 5 to 7 carbon atoms and M stands for a cation.  Such compounds are obtained by reacting an alkali metal sulphite or bisulphite with halogenohydrins of a monoalkyl ether of glycerine which contains 5 to 7 carbon atoms in the alkyl group, or on the corresponding epoxides.  The reaction may be effected with such proportions of reactants that only a portion of the halogenhydrin or epoxide is converted into the corresponding alkali metal salts of the sulphonic acids, and the portion of halohydrin or epoxide which is not converted may be hydrolysed or hydrated, giving ether alcohols which inhibit crystallization of the other component of the product, the sulphonic acids and their salts.  The halogenohydrins can be obtained by reacting such alcohols as isoamyl, 2- or 3-amyl, n-hexyl, 2-ethylbutyl, methylamyl or 3-heptyl alcohol or their mixtures with epichlorhydrin to give the chlorhydrins, from which the epoxides are obtainable by treatment with hydrochloric acid.  Preferably the halogenhydrins are reacted with neutral sulphites and the epoxides with bisulphites.  The products, which are of use in textile-treatment solutions (see Group IV (c)) may be mixed with ether-alcohols of glycol, polyglycols, glycerine and polyglycerine (e.g. the product obtained by reacting 2 or more mols. of epichlorhydrin with one mol. of butyl, amyl or hexyl alcohol followed by boiling with dilute caustic soda solution).  There may also be added phenols or naphthenic acids, aliphatic or cycloaliphatic hydrocarbons, e.g. those of boiling-point 150 DEG  to 250 DEG  C., alcohols such as those containing 5 to 12 carbon atoms in the molecule, or, to diminish the foaming properties, trialkyl esters of phosphoric acid and organic silicon compounds.  In examples: (1) epichlorhydrin and isoamyl alcohol are reacted in the presence of a boron trifluoride/ether complex to give a product of the formula <FORM:0751244/IV(a)/1> as main product, together with a compound of the formula <FORM:0751244/IV(a)/2> Reaction of the crude epoxide with sodium bisulphite gives the sodium salt of isoamyloxypropanol sulphonic acid of the formula (CH3) 2CH-CH2-CH2-O-CH2-CHOH-CH2 -SO3Na, together with the isoamyl ether of glycerine and of diglycerine; (2) the corresponding n-amyloxy compound is prepared; (3) 2-pentyloxychloropropanol obtained by reacting 2-pentanol with epichlorhydrin is reacted with sodium sulphite to give the sodium salt of 2-pentyloxypropanol sulphonic acid of formula C3H7CH(CH3)OCH2CHOH.CH2SO3Na. The reaction may be effected in the presence of diethyleneglycol mono-n-butyl ether; (4) 1 mol. of an amyl alcohol mixture is reacted with 1.4 mols. of epichlorhydrin, the crude chlorhydrin obtained is treated with caustic soda, and the chlorine-containing epoxide mixture produced is condensed with 0.8 mols. of sodium bisulphite and the product refluxed with 0.5 mols. of 30 per cent caustic soda solution; (5) methylamyloxychloropropanol (from the reaction of methylisobutylcombinol with epichlorhydrin) is treated with caustic soda lye to give methylisoamyloxypropenoxide which on reaction with sodium bisulphite gives the sodium salt of methylamyloxy-propanol sulphonic acid.  Treatment with barium or chloride gives the corresponding barium salt from which the barium can be removed as sulphate by treatment with sulphuric acid; (6) methylamyloxypropenoxide chlorine-containing products (obtained by reacting methylamyl alcohol with epichlorhydrin, followed by treatment with caustic soda) is treated with sodium bisulphite and sodium carbonate solution to give a mixture of methylamyloxypropanol sulphonic acid sodium salt, the methylamyl ethers of glycerine, and diglycerine.  Hexylene-glycol and diisobutyl carbinol may be added; (7) 2-ethylbutanol may be used in reactions similar to (6) to give the sodium salt of 2-ethylbutyloxypropanol sulphonic acid together with glycerine ethers; (8) heptanol-3 is reacted similarly, to give 3-heptyloxypropanol sulphonic acid sodium salt with intermediate formation of the propenoxide.  Hexaethyleneglycol monododecyl ether may be added to the product.ALSO:Wetting agents particularly suitable in alkaline treatment baths for textiles, such as those used in mercerizing and alkalizing cellulose and regenerated cellulose, comprise compounds obtained by reacting an alkali metal sulphite or bisulphite with a halogenhydrin of a monalkyl ether of glycerine which contains from 5 to 7 carbon atoms in the alkyl group, or with the corresponding epoxide.  The agents have as their main component compounds of the formula R-O-CH2-CHOH-CH2-SO3M where R stands for an alkyl radical containing 5 to 7 carbon atoms and M is a cation. The preparation of such agents is described in detail (see Group IV(b)). There may also be present in the wetting agent ether-alcohols (formed in the same reaction mixture with the sulphonates or added afterwards) such as mono ethers of glycol, polyglycols, glycerol and polyglycerol.  As further auxiliary agents there may be added phenols or naphthenic acids, aliphatic or cycloaliphatic hydrocarbons such as those of boilingpoint 150 DEG  to 250 DEG C., alcohols having 5 to 12 carbon atoms in the molecule and (to diminish foaming) trialkyl phosphates and organic silicon compounds.  Examples describe (2) a mercerizing solution of 28 DEG  B<\>ae. containing the sodium salt of n-amyloxypropanol sulphonic acid; (5) the shrinking of crude cotton yarn by treatment with caustic lyes of 20 to 32 DEG  B<\>ae. containing the sodium salt of methyl amyloxy-propanol sulphonic acid, with and without the addition of diethylene - glycol - mono - n - butyl ether; (7) the treatment of undesized grey cloth with a mercerizing solution of 28 DEG  B<\>ae. containing the sodium salt of 2 - ethylbutyloxypropanol sulphonic acid; (8) the use as a wetting agent for caustic soda lye of 5 DEG  B<\>ae., as used in the preparation of artificial silk crepe, of the sodium salt of 3 - heptyloxypropanol sulphonic acid together with hexaethyleneglycol mono - dodecylether.