Patent GB-688536-A (GB)
Title: Improvements in the manufacture and use of sulphonic acid esters
Inventor: HELBERGER JOHANN HEINRICH
IPC: C09D115/00
Filed: 1949-07-09
Abstract: Polymerized organic substances are plasticized by incorporating therewith a sulphonic acid ester containing no free sulphonic acid group prepared by reacting a phenol with an alkyl or cycloalkyl benzene sulphochloride having at least one alkyl or cycloalkyl group of at least ten carbon atoms (see Group IV (b)). Polymerized organic substances mentioned include phenol plastics, amino plastics, cellulose derivatives, polyvinyl compounds, polyamides and polyurethanes.  In examples: (3) an alkyl benzene sulphonic acid phenyl ester, prepared from a benzene sulphonyl chloride alkylated with aliphatic hydrocarbons containing 10-14 carbon atoms in the molecule, is added to a solution of nitrocellulose in butyl acetate, xylene and butanol; (4) a copolymer of vinyl acetate and vinyl chloride is homogenized with an ester prepared from dodecyl benzene sulphochloride and phenol; (5) a copolymer of vinyl acetate and vinyl chloride is dissolved in ethyl acetate, xylene and acetone and an alkyl benzene sulphonic acid cresyl ester containing in the alkyl chain ten carbon atoms is added; (6) polyvinyl chloride is plasticized with the ester employed in example (4).ALSO:In a process for the manufacture of sulphonic acid esters containing no free sulphonic acid groups an alkyl or cyclo-alkyl benzene sulphochloride with at least one alkyl or cycloalkyl group having at least 10 carbon atoms is treated with a phenol preferably in the presence of acid binding means and/or inert solvents.  Polymerized organic substances may be plasticized by incorporating therewith a sulphonic acid ester of the invention. The alkyl benzene sulphochlorides may contain one or more straight or branched chains containing at least ten carbon atoms and examples mentioned are cetyl, dodecyl, hexadecyl and octadecyl. Cycloaliphatic groups mentioned are dicyclopentyl and residues of alkyl-cyclohexanes or other perhydrogenated araliphalic compounds which may be united to the benzene nucleus either through the aliphatic or hydroaromatic part.  Alkyl or cycloalkyl benzene sulphochlorides containing in the benzene nucleus more than one sulphochloride group may be employed.  Alkyl benzene sulphochlorides may be produced for example by chlorinating a natural or synthetic hydrocarbon with a chain length of about ten to eleven carbon atoms to introduce one chlorine atom per hydrocarbon molecule and reacting the product with benzene in the presence of aluminium chloride.  The alkyl benzene obtained is sulphonated and converted to the sulphochloride by means, e.g. of chlorosulphonic acid or phosphorus pentachloride.  Phenols suitable as starting materials include phenol, cresols, xylenols and naphthols.  Acid binding means may be added to the mixture of reactants or may be combined with the phenol, e.g. as in phenolates.  Esters are produced on reacting in examples: (1) dodecyl benzene sulphochloride and phenol in caustic soda solution; (2) decahydronaphthalene sulphochloride, obtained by chlorinating decahydronaphthalene, isolating the monochlordecahydronaphthalene formed, condensing it with benzene in the presence of aluminium chloride and introducing a sulphochloride group into the benzene nucleus and phenol; (3) an alkyl benzene sulphonic acid prepared by chlorinating a mixture of synthetic aliphatic hydrocarbons, obtained by the reaction between carbon monoxide and hydrogen containing 10-14 carbon atoms in the molecule, isolating the monochlorinated hydrocarbons, condensing this mixture with benzene, introducing a sulphochloride group into the benzene nucleus and reacting the product with phenol and in example (5) an alkyl benzene sulphonic acid cresyl ester containing ten carbon atoms in the alkyl chain is similarly prepared.  The products of the invention are suitable as textile assistants and for leather treatment and may be used as swelling, plasticizing and gelatinizing media for phenol plastics, amino plastics, cellulose derivatives, polyvinyl compounds, polyamides and polyurethanes (see Group IV (a)), and may be employed in paper-treating compositions and chlorinated rubber compositions (see Group V).ALSO:Chlorinated rubber may be plasticised with a sulphonic acid ester containing no free sulphonic acid groups obtained by reacting an alkyl or cycloalkyl benzene sulphochloride, with at least one alkyl or cycloalkyl group having at least ten carbon atoms, with a phenol (see Group IV (b)).  In example 7 a composition comprises chlorinated rubber, xylene, tetrahydronaphthalene and an alkyl benzene sulphonic acid phenyl ester of which the alkyl chain has from ten to twelve carbon atoms prepared according to the process of the invention.