Patent GB-358583-A (GB)
Title: Improvements in the manufacture and production of wetting, cleansing and dispersing agents
IPC: D06M13/256
Filed: 1930-07-11
Abstract: True sulphonic acids derived from olefines containing at least eight carbon atoms in the molecule and a double linkage at the end of the chain, by treatment with strong liquid sulphonating agents, are used as emulsifying and dispersing agents.  Strong, liquid sulphonating agents are defined as liquid sulphonating agents stronger than sulphuric acid, and include chlorsulphonic acid, or solutions of sulphur trioxide in either sulphuric acid, chlorsulphonic acid, sulphur dioxide or inert organic solvents; the agents also include mixtures of liquid, mild sulphonating agents, with water removing substances, e.g. acetic, boric, phosphoric or butyric anhydride or phosphorus trichloride or acetylchloride.  The sulphonation is continued until the product remains soluble or miscible with water, on boiling with aqueous 10 per cent hydrochloric acid.  Besides the sulphonic group, which is united to the end or penultimate carbon atom, another acid residue, e.g. acetic or sulphuric acid, residue or chlorine, depending upon the sulphonating agent employed is simultaneously attached to the double bond.  It is removed however by heating with water, acids or alkalies, with ormation of a hydroxy group or a double bond.  The products may be employed with the usual wetting, cleansing, emulsifying, and dispersing agents, such as saponin, sulphonic acids, sulphuric esters and soaps.  In examples (1) octadecyl alcohol is esterified with phosphoric acid and octadecylene, which is obtained by distilling the product, is sulphonated with sulphuric acid and acetic anhydride; the product is probably hydroxyoctadecylsulphonic acid, (2) a mixture of olefines obtained by distilling the phosphoric esters of the alcohols obtained by the catalytic hydrogenation of coco nut fat is sulphonated in ether with chlorsulphonic acid; (3) octadecylene is sulphonated with oleum; (4) a mixture of sulphuric acid and acetic anhydride is used to sulphonate octodecadiene which may be obtained by splitting off water from octodecandiol, the product obtained by the catalytic reduction of castor oil. Suitable olefines may also be obtained from the alcohol obtained by the catalytic reduction of olive oil and by distilling the esters of alcohols of high molecular weight with the acids of fats and oils.  Specifications 303,917 and 306,052, [both in Class 2 (iii), Dyes &c.], are referred to.ALSO:Olefines containing at least eight carbon atoms in the molecule, and a double linkage at the end of the chain are sulphonated with strong liquid sulphonating agents, whereby true sulphonic acids are obtained.  Strong, liquid sulphonating agents are defined as liquid sulphonating agents stronger than sulphuric acid, and include chlorsulphonic acid, solutions of sulphur trioxide in sulphuric acid, chlorsulphonic acid, sulphur dioxide or inert organic solvents, and also mixtures of liquid, mild sulphonating agents with water removing substances, e.g. acetic, boric, phosphoric or butyric anhydride or phosphorus trichloride or acetyl chloride.  By using the diluents, e.g. carbon tetrachloride, nitrobenzene, trichlorethylene, ethylacetate or ether, gaseous sulphur trioxide may be used, the liquid strong sulphonating agent being then formed in situ.  Known sulphonating catalysts, such as diatomaceous earth, animal charcoal, boric acid, silver or mercury sulphate may be used.  The sulphonation is continued until the product remains soluble or miscible with water, on boiling with aqueous 10 per cent hydrochloric acid. Besides the sulphonic group, which is united to the end or penultimate carbon atom, another acid residue, e.g. acetic or sulphuric acid residue, or chlorine, depending upon the sulphonating agent employed is simultaneously attached to the double bond.  It is removed however by heating with water, acids or alkalies, with formation of a hydroxy group or a double bond. The products are stated to be wetting, cleansing, emulsifying, dispersing, softening and levelling agents and may be used in the leather, textile, e.g. artificial silk, industries.  The usual auxiliary agents, such as saponin, sulphonic acids, sulphuric esters and soaps may be used therewith.  In examples (1) octadecyl alcohol is esterified with phosphoric acid and octadecylene, which is obtained by distilling the product, is sulphonated with sulphuric acid and acetic anhydride; the product is probably hydroxyoctadecylsulphonic acid; (2) a mixture of olefines obtained by distilling the phosphoric esters of the alcohols obtained by the catalytic hydrogenation of coconut fat is sulphonated in ether with chlorsulphonic acid; (3) octadecylene is sulphonated with oleum; (4) a mixture of sulphuric acid and acetic anhydride is used to sulphonate octodecadiene which may be obtained by splitting off water from octodecandiol, the product obtained by the catalytic reduction of castor oil.  Suitable olefines may also be obtained from the alcohol obtained by the catalytic reduction of olive oil and by distilling the esters of alcohols of high molecular weight with the acids of fats and oils. Specifications 303,917 and 306,052, [both in Class 2 (iii), Dyes &c.], are referred to.