Patent GB-734191-A (GB)
Title: Process for the manufacture of sulphonation products including textile treating agents
IPC: C07B45/02
Filed: 1952-01-23
Abstract: Surface-active compounds are prepared by the sulphonation of non-heterocyclic compounds containing a primary or secondary alcohol group and having at least 6 carbon atoms in the molecule, with the reaction product of chlorsulphonic acid on an acid amide containing not more than 6 carbon atoms or a mixture of such amides, the amount of acid amide or mixture thereof used being at least 1.3 mols. per mol. of chlorsulphonic acid (see Group IV (b)).  Suitable amides are carboxylic and sulphonic acid amides, urea, alkyl ureas and other urea derivatives, for example formamide, acetamide, diacetamide, malonic acid amide, methane sulphonamide, butane sulphonamide, benzene sulphonamide and amino or ureido sulphonic acid amides.  The alcoholic compounds treated may be aliphatic, cycloaliphatic or aromatic; atoms other than carbon, e.g. N, S or O may be present in the chains to which the hydroxyl groups are attached or in substituents on these chains, e.g. carboxylic acid, amide or ester radicals or sulphonic acid or amide radicals.  The neutralized sulphonation products are paste-like and yield clear aqueous solutions having foaming, washing, cleaning, wetting and dispersing properties; they find use in the leather and textile industries, e.g. in treating wool, cotton, silk, cellulose rayon, and other synthetic fibre materials.  Examples describe the sulphonation of oleyl alcohol, sperm oil alcohols, C13-17 alcohols obtained by hydrogenation of ketones prepared by ketonizing C7-9 acids formed by oxidation of paraffins, butyl ricinoleate, castor oil and castor oil fatty acids, using as sulphonating agent the reaction products of urea and/or formamide with chlorsulphonic acid or of urea with SO3 and hydrogen chloride, the mol. ratio of amide being from 1.3 up to about 4 per mol. of acid. Other specified alcoholic reactants are alcohols obtained by hydrogenation of fatty acids or esters, e.g. castor or linseed oil, or of acids obtained by oxidation of paraffins, Oxo alcohols, sec.-hexyl, octyl and octadecyl alcohols, cyclohexanols, ricinoleic acid and its alkyl esters, and alcohols obtained by the splitting or hydrogenolysis of animal waxes. According to examples of the use of the products: (13) and (15) textile materials, e.g. wool, are washed in an aqueous bath containing sulphonated oleyl alcohol; (14) a similar bath is used for defatting artificial silk goods; (16) goods dyed with naphthalene dyestuffs are after-soaped in an aqueous bath containing sulphonated sperm oil alcohols; (17) stockings are uniformly dyed by means of a dye bath containing a sulphonated oleyl alcohol. Specification 621,618 is referred to.ALSO:Surface-active compounds are prepared by the sulphonation of non-heterocyclic compounds containing a primary or secondary alcohol group and having at least 6 carbon atoms in the molecule, with the reaction product of chlorsulphonic acid on an acid amide containing not more than 6 carbon atoms or a mixture of such amides, the amount of acid amide or mixture thereof used being at least 1.3 mols. per mol. of chlorsulphonic acid.  Suitable amides are carboxylic and sulphonic acid amides, urea, alkyl ureas and other urea derivatives, for example formamide, acetamide, diacetamide, malonic acid amide, methane sulphonamide, butane sulphonamide, benzene sulphonamide and amino or ureido sulphonic acid amides.  The formation of the sulphonating agent (termed an addition compound) is effected by reacting chlorsulphonic acid with the amide while cooling to prevent the temperature exceeding 60 DEG  C.  The urea addition compound may also be formed using sulphur trioxide and hydrogen chloride.  The sulphonation is normally effected by kneading together the hydroxy compound and sulphonating agent at about 20-80 DEG  C.; the product is neutralized by kneading with an alkali.  The alcoholic compounds treated may be aliphatic, cycloaliphatic or aromatic; atoms other than carbon, e.g. N, S or O, may be present in the chains to which the hydroxyl groups are attached or in substituents on these chains, e.g. carboxylic acid, amide or ester radicals or sulphonic acid or amide radicals.  The neutralized sulphonation products are paste-like and yield clear aqueous solutions having foaming, washing, cleaning, wetting and dispersing properties; they find use in the leather and textile industries (see Group IV (c)). Examples describe the sulphonation of oleyl alcohol, sperm oil alcohols, C13-17 alcohols obtained by hydrogenation of ketones prepared by ketonizing C7-9 acids formed by oxidation of paraffins, butyl ricinoleate, castor oil and castor oil fatty acids, using as sulphonating agent the reaction products of urea and/or formamide with chlorsulphonic acid or of urea with SO3 and hydrogen chloride, the mol. ratio of amide being from 1.3 up to about 4 per mol. of acid.  Other specified alcoholic reactants are alcohols obtained by hydrogenation of fatty acids or esters, e.g. castor or linseed oil, or of acids obtained by oxidation of paraffins, Oxo alcohols, sec.-hexyl, octyl and octadecyl alcohols, cyclohexanols, ricinoleic acid and its alkyl esters, and alcohols obtained by the splitting or hydrogenolysis of animal waxes. Specification 621,618 is referred to.