Patent GB-415877-A (GB)
Title: Manufacture of textile adjuvants
Filed: 1933-07-15
Abstract: Products useful as washing and dispersing agents are prepared by converting into sulphonic acids or sulphuric acid esters (or salts of either of these) sulphones of the formula RSO2R<1>, where R is an aromatic or aliphatic-aromatic radicle and R<1> is an aliphatic radicle containing at least eight carbon atoms, which may be substituted.  Sulphones for use as starting materials may be prepared by reacting an alkali salt of a sulphinic acid of the benzene toluene, or a - or b -naphthalene series, or benzyl-sulphinic acid, with chlorotetradecane cetyl iodide or other halogenated paraffin containing at least eight carbon atoms, or with an a -halogen fatty acid containing at least eight carbon atoms or a derivative thereof, e.g. the ethyl ester of a -bromo-lauric or a -bromostearic acid. Sulphones containing a hydroxy group may be prepared by converting a phenol carbonate into a sulphinic acid in known manner and condensing the product, or the hydroxysulphinic acid obtained therefrom by saponification, with an aliphatic halogen compound containing at least eight carbon atoms.  If the starting materials for the preparation of the sulphone do not contain a sulphonic or sulphuric acid ester group, the sulphone may be treated with a sulphonating agent.  The products may be used alone or with solvents, protective colloids or soaps, in the textile and leather industries.  In the examples, (1) sodium p-toluenesulphinate is heated in ethyl alcohol with a mixture of higher aliphatic chlorides sold under the name " Lorylchloride " and the product is sulphonated; (2) sodium p-toluenesulphinate is heated in ethyl alcohol with a -bromolauric acid ethyl ester, and the product is sulphonated.  A sample has been furnished under Sect. 2 (5) of a product prepared as follows:--sodium benzylsulphinate is heated in ethyl alcohol with lauryl iodide, and the product is sulphonated.  The Specification as open to inspection under Sect. 91 states that R in the formula above may be an aliphatic or cycloaliphatic radicle and R<1> a cycloaliphatic radicle, and refers to the preparation of sulphones from ethanesulphinic acid and " camphenesulphinic acid-(2)."  It states also that water-soluble sulphone derivatives may be obtained by treating a salt of a sulphinic-sulphonic acid, such as naphthalene-1-sulphinic-4-sulphonic acid, with an organic halogen compound such as cetyl chloride or a -bromolauric acid ethyl ester.  Further, it includes an example in which sodium p-toluene-sulphinate is heated in ethyl alcohol with a -bromostearic acid ethyl ester, and the product is sulphonated. This subject-matter does not appear in the Specification as accepted.ALSO:Products useful as wetting, washing and dispersing agents are prepared by converting into sulphonic acids or sulphuric acid esters (or salts of either of these) sulphones of the formula RSO2R<1>, where R is an aromatic or aliphatic-aromatic radicle and R<1> is an aliphatic radicle containing at least eight carbon atoms, which may be substituted.  Sulphones for use as starting materials may be prepared by reacting an alkali salt of a sulphinic acid of the benzene, toluene, or a - or b -naphthalene series, or benzylsulphinic acid, with chlorotetradecane, cetyl iodide or other halogenated paraffin containing at least eight carbon atoms, or with an a -halogen fatty acid containing at least eight carbon atoms or a derivative p  thereof, e.g. the ethyl ester of a -bromolauric or a -bromostearic acid.  Sulphones containing a hydroxy group may be prepared by converting a phenol carbonate into a sulphinic acid in known manner and condensing the product, or the hydroxysulphinic acid obtained therefrom by saponification, with an aliphatic halogen compound containing at least eight carbon atoms.  If the starting materials for the preparation of the sulphone do not contain a sulphonic or sulphuric acid ester group, the sulphone may be treated with a sulphonating agent, e.g. sulphuric acid, sulphur trioxide, a sulphuric acid halohydrin, or mixtures of any of these; this reaction may be effected in the presence of a solvent or diluent, e.g. acetic acid, or a dehydrating agent, e.g. acetic anhydride or phosphorus pentoxide. Alternatively, a sulphone containing halogen may be treated with a sulphite.  The products may be used, alone or with solvents, protective colloids or soaps, in the textile and leather industries.  In the examples: (1) sodium p-toluenesulphinate is heated in ethyl alcohol with a mixture of higher aliphatic chlorides sold under the name "lorylchloride," and the product is sulphonated with fuming sulphuric acid; the sulphonated product may be used for washing wool or wetting cotton or wool yarn; (2) sodium p-toluenesulphinate is heated in ethyl alcohol with a -bromolauric acid ethyl ester, and the product is sulphonated with chlorosulphonic and fuming sulphuric acids.  A sample has been furnished under Sect. 2 (5) of a product prepared as follows:--sodium benzylsulphinate is heated in ethyl alcohol with lauryl iodide, obtainable by treating "lorylchloride" with sodium iodide in acetone; the product is then sulphonated with sulphuric acid containing sulphur trioxide.  The Specification as open to inspection under Sect. 91 states that R in the formula above may be an aliphatic or cycloaliphatic radicle and R<1> a cycloaliphatic radicle, and refers to the preparation of sulphones from ethanesulphinic acid and "camphenesulphinic acid-(2)." It states also that water-soluble sulphone derivatives may be obtained by treating a salt of a sulphinic-sulphonic acid, such as naphthalene-1-sulphinic-4-sulphonic acid, with an organic halogen compound such as cetyl chloride or a -bromolauric acid ethyl ester. Further, it includes an example in which sodium p-toluenesulphinate is heated in ethyl alcohol with a -bromostearic acid ethyl ester, and the product is sulphonated with chlorosulphonic and fuming sulphuric acids.  This subject-matter does not appear in the Specification as accepted.