Patent GB-455694-A (GB)
Title: Improvements in or relating to new sulphonamide compounds
IPC: C08K5/43
Filed: 1935-04-27
Abstract: Aromatic sulphonamides containing one or more N-monohydroxyalkyl groups acidylated at the oxygen atom with a carboxylic acid radicle are prepared (a) by treating a N-monohydroxyalkyl aromatic sulphonamide with an appropriate acidylating agent or (b) by treating an aromatic sulphonamide with an appropriate alkylating agent, e.g. with a carboxylic ester of a halogenated alcohol, such as chlorethyl acetate.  The sulphonamides taken as starting materials may be of the benzene series or of the naphthalene or other polynuclear series; they may be further substituted, e.g. by methyl, ethyl or other alkyl groups, acidylamino or hydroxy groups, or halogen atoms.  The products may contain one or more esterified N-monohydroxyalkyl groups; when only one such group is linked to the nitrogen atom of a sulphonamide group, another substituent, e.g. a methyl, ethyl or other alkyl group, or a hydroxyethyl or other hydroxyalkyl group, may also be linked to the nitrogen atom; the groups linked to the nitrogen atom may be further substituted, e.g. by halogen, but the ester group or groups in the products must be linked to the nitrogen atom solely by carbon atoms.  Products containing a free hydroxy group may be converted into phosphoric esters, this yielding products having a fire-retarding action.  Specified sulphonamides for treatment by method (a) above are N-mono- and di-(monohydroxyalkyl)-benzene, -toluene, -xylene and -naphthalene sulphonamides, particularly N-mono- or di-(monohydroxyethyl)-benzene, -toluene and -xylene sulphonamides and N-(chlorohydroxypropyl) - benzenesulphonamide; these substances are obtainable from the appropriate aromatic sulphonamides and hydroxyalkylating agents; thus, N-mono- and di-(monohydroxyethyl)-p-toluenesulphonamide are obtainable from p-toluenesulphonamide and ethylene chlorhydrin in the presence of aqueous acustic soda, and the corresponding benzenesulphonamide compounds are similarly obtainable; N - (chlorohydroxypropyl) - benzenesulphonamide is obtainable from benzenesulphonamide and epichlorhydrin.  Acidylating agents for use in method (a) above are carboxylic acids and their anhydrides or chlorides, and specifically acetic acid, acetic anhydride, lactic acid, benzoic acid, phthalic acid and phthalic anhydride.  The products are useful as constituents of cellulose derivative compositions or plastic compositions having a basis of synthetic resin, rubber or like material; cellulose derivatives specified in this connection are cellulose formate, acetate, propionate, butyrate, nitrate or other cellulose ester, or methyl, ethyl or benzyl cellulose or other cellulose ether; synthetic resins specified are polyvinyl acetate or other polyvinyl resins.  The products containing one N-monohydroxyalkyl group esterified with a mono- or polycarboxylic acid, and the products containing more than one N-monohydroxyalkyl group esterified with a monocarboxylic acid, are generally useful as plasticizers; the products containing two or more N-monohydroxyalkyl groups esterified with a polycarboxylic acid are generally resins compatible with cellulose derivatives. Compositions containing the products and cellulose derivatives may be prepared as solutions or solid mixtures; solutions in volatile solvents, such as acetone, with or without other additions such as other plasticizers, medium- or high-boiling solvents, natural or synthetic resins, fire-retardants and effect materials, may be used as coating or impregnating compositions or adhesives, or in the manufacture of filaments or films; solid mixtures useful as moulding powders may be produced by causing a finely divided cellulose derivative to absorb the plasticizer from a solution or dispersion, or by precipitating the plasticizer from solution on to the cellulose derivative; such solid mixtures may be moulded by pressure or injection, or worked into sheets for use in making nonsplintering glass.  In examples of the preparation of the sulphonamide derivatives, N - mono- or di - (monohydroxyethyl) - p - toluenesulphonamide is (1) boiled with acetic anhydride and acetic acid, and (2) heated to 200 DEG  C. with phthalic anhydride; the products of example 2 are resins.  In examples of compositions containing the products, (3) cellulose acetate is stirred in water with a product of example 1, with or without a product of example 2, and the mixture is filtered and dried; the products are useful as moulding powders; (4) solutions suitable for making films are prepared from (a) cellulose acetate, acetone, and a product of example 1, and (b) cellulose acetate, products of examples 1 and 2, acetone, benzene, alcohol and diacetone alcohol; (5) a lacquer for coating electric cables contains cellulose acetate, a product of example 1, acetone, alcohol, and benzene; (6) a lacquer for coating metals contains cellulose acetate, diphenylolpropane-formaldehyde resin, a product of example 1, acetone, methylethyl ketone, alcohol, benzene, toluene, ethyl lactate, and the substance sold under the Registered Trade Mark "Methyl Cellosolve."  The Provisional Specification states that esterified N-hydroxyalkyl aryl sulphonamides may be prepared (a) by condensing an aromatic sulphohalide, e.g. benzenesulphochloride, with an aminoalkyl ester, e.g. aminoethyl acetate, or (b) by treating an aromatic sulphonamide with an aliphatic compound, such as glycide acetate, containing an ester group and a group capable of reaction with an amino group.  It refers also to the manufacture of esters of N-(polyhydroxyalkyl) aryl sulphonamides.ALSO:Aromatic sulphonamides containing one or more N-monohydroxyalkyl groups acidylated at the oxygen atom with a carboxylic acid radicle are used as constituents of rubber compositions.  The sulphonamides taken as starting materials may be of the benzene series or of the naphthalene or other polynuclear series and may be further substituted, e.g. by methyl, ethyl or other alkyl groups, acidylamino or hydroxy groups, or halogen atoms.  The products may contain one or more esterified N-monohydroxyalkyl groups; when only one such group is linked to the nitrogen atom of a sulphonamide group, another substituent, e.g. a methyl, ethyl or other alkyl group, or a hydroxyethyl or other hydroxyalkyl group, may also be linked to the nitrogen atom; the groups linked to the nitrogen atom may be further substituted, e.g. by halogen, but the ester group or groups in the products must be linked to the nitrogen atom solely by carbon atoms. Products containing a free hydroxy group may be converted into phosphoric esters, this yielding products having a fire-retarding action. Specified sulphonamides are O-acylated N-mono- and di-(monohydroxyalkyl)-benzene, -toluene, -xylene and -naphthalene sulphonamides, particularly N-mono-or di-(monohydroxyethyl)-benzene, -toluene and -xylene sulphonamides and N-(chlorohydroxypropyl)-benzenesulphonamide.  Acidylating agents specified are acetic acid, acetic anhydride, lactic acid, benzoic acid, phthalic acid and phthalic anhydride.  The products containing one N-monohydroxyalkyl group esterified with a mono- or poly-carboxylic acid, and the products containing more than one N-monohydroxyalkyl group esterified with a monocarboxylic acid, are generally useful as plasticizers; the products containing two or more N-monohydroxyalkyl groups esterified with a polycarboxylic acid are generally resins.  The Provisional Specification refers also to the use of esters of N-(polyhydroxyalkyl) aryl sulphonamides.