Patent GB-381204-A (GB)
Title: Improvements in the manufacture and production of wetting, cleansing and dispersing agents
IPC: D06M13/425
Filed: 1931-06-25
Abstract: Sulphonated urethanes, stated to be assistants for the textile, paper, leather and lacquer industries, are obtained by treating with sulphonating agents, urethanes containing at least five carbon atoms and at least one double linkage, hydroxy group or aromatic nucleus. The products, which may be used alone or in association with, soaps, soap like substances, salts, e.g. Glauber's salt, or Epsom salt, hypochlorites, perborates, glue, gum arabic or gelatine are wetting, washing, emulsifying, levelling and softening agents, and may be used as additions in printing pastes and in carbonizing, mercerizing, spinning and dye baths, and also for fulling, dressing and softening textiles, e.g. artificial silk.  Lubricants, boring oils and polishing agents may be prepared by using the products as emulsifying agents; emulsions of waxes, oils, fats, solvents and dyestuffs may thus be prepared.  In examples, (1) a urethane obtained from the chlorcarbonic ester of octodecyl alcohol and n-butanolamine is sulphonated, in ether or carbontetrachloride, with chlorsulphonic acid: (2) a urethane obtained from laurylchlorcarbonicester and ethanolamine is sulphonated with sulphuric acid, and the product precipitated by means of butylacetate: (3) the urethane from benzylchlorcarbonicester and N-cyclohexyl-N-ethanolamine is sulphonated, in carbontetrachloride with chlorsulphonic acid: (4) the urethane obtained by treating aniline in caustic soda with octodecylchlorcarbonicester is sulphonated with sulphuric acid: (5) the urethane obtained from oleylchlorcarbonicester and ethanolamine is sulphonated, in ethylenechloride with chlorsulphonic acid: (6) cyclohexanolchlorcarbonicester is condensed with N-cyclohexyl-N-ethanolamine and then sulphonated: (7) oleylchlorcarbonicester is condensed with n-butylamine and then sulphonated with sulphuric acid to give a sulphuric ester: (8) the urethane from oleylchlorcarbonicester and ammonia is treated with chlorsulphonic acid, in carbontetrachloride to obtain a urethane containing a hydroxy group and a sulphonic group in the alcoholic radicle: (9) the urethane from n-butylalcohol and ethanolamine is sulphonated: (10) the urethane from phenolchlorcarbonicester and propanolamine is treated with sulphuric acid.  The urethanes may be prepared by condensing ammonia or primary or secondary amines containing one or more nitrogen atoms with chlorcarbonic esters of polyhydric alcohols or mono or polyhydric phenols, or by condensing primary or secondary hydroxyalkylamines or aromatic amines with chlorcarbonic esters of monohydric alcohols.  The hydroxy alkylurethanes may be treated with alkyleneoxides before use.  Oleum and sulphur trioxide may be used as the sulphonating agent.  The chlorcarbonic esters used in the examples may be prepared by treating the appropriate alcohol with phosgene.ALSO:Sulphonated urethanes, or their alkali metal or alkaline-earth salts, prepared by treating urethanes containing at least five carbon atoms and at least one double linkage, hydroxy group or aromatic nucleus with sulphonating agents, are stated to be washing and emulsifying agents.  They may be used alone or in association with soaps, soap-like substances, salts, e.g. Glauber's salt or Epsom salt, hypochlorites, perborates, glue, gelatine, gum arabic or gelatine, and may be used for the production of lubricants, boring oils, and polishing agents; emulsions of waxes, oils, fats, and solvents may also be prepared. In examples (1) a urethane obtained from the chlorcarbonic ester of octodecyl alcohol and n-butanolamineissulphonated, in ether or carbontetrachloride, with chlorsulphonic acid: (2) a urethane obtained from lauryl chlorcarbonic ester and ethanolamine is sulphonated with sulphuric acid, and the product precipitated by means of butylacetate: (3) the urethane from benzyl chlorcarbonic ester and N-cyclohexyl-N-ethanolamine is sulphonated in carbontetrachloride with chlorsulphonic acid: (4) the urethane obtained by treating aniline in caustic soda with octodecylchlorcarbonic ester is sulphonated with sulphuric acid: (5) the urethane obtained from oleylchlorcarbonic ester and ethanolamine is sulphonated in ethylenechloride with chlorsulphonic acid: (6) cyclohexanol-chlorcarbonic ester is condensed with N-cyclohexyl-N-ethanolamine and then sulphonated: (7) oleyl-chlorcarbonic ester is condensed with n-butylamine and then sulphonated with sulphuric acid to give a sulphuric ester: (8) the urethane from oleylchlorcarbonic ester and ammonia is treated with chlorsulphonic acid in carbon tetrachloride to obtain a urethane containing a hydroxy group and a sulphonic group in the alcoholic radicle: (9) the urethane from n-butylalcohol and ethanolamine is sulphonated: (10) the urethane from phenol-chlorcarbonic ester and propanolamine is treated with sulphuric acid.  The urethanes may be prepared by condensing ammonia or primary or secondary amines containing one or more nitrogen atoms with chlorcarbonic esters of polyhydric alcohols or mono or polyhydric phenols, or by condensing primary or secondary hydroxyalkylamines or aromatic amines with chlorcarbonic esters of monohydric alcohols.  The hydroxyalkylurethanes may be treated with alkyleneoxides before use.