Patent GB-483087-A (GB)
Title: Improvements in or relating to condensation products for aromatic sulphonamides and to the use of the products in plastic compositions
IPC: C08K5/43
Filed: 1936-10-12
Abstract: Condensation products are manufactured by reacting a non-hydroxylated aromatic sulphonamide with a dihalogenhydrin, and, if desired, acylating, alkylating or aralkylating the products.  The sulphonamides may be mono- or polynuclear, and may contain nuclear substituents other than hydroxy groups, e.g. alkyl groups such as methyl or ethyl, acidylamino groups or halogen atoms, whilst one of the hydrogen atoms of the amide group may be replaced, e.g. by an alkyl or aralkyl group.  The condensation, in which equal or unequal molecular proportions of the reactants may be employed, is advantageously effected in the presence of alkali.  In examples: (1) p-toluene-sulphonamide is dissolved in aqueous caustic soda solution and the solution is refluxed with an equimolecular proportion of symm. glycerol dichlorhydrin; (2) twice as much p-toluene-sulphonamide is used in the process of (1); (3) the product of (2) is heated with acetic anhydride.  Other reactants specified are: sulphonamides: benzene, naphthalene, o-toluene and xylene sulphonamides; dichlorhydrins: asymm. glycerol dichlorhydrin and dichlorosec.-butyl alcohols; acylating agents: organic acids, their anhydrides and chlorides, e.g. phthalic anhydride, phenylacetic acid and phenoxyacetic acid; alkylating agents: methyl chloride and diethyl sulphate.  Specification 455,694 is referred to.  The Provisional Specification comprises also the use of polyhalogenhydrins.  A sample has been furnished under Sect. 2 (5) of the product obtained by heating the product of (2) above with dimethyl sulphate and aqueous caustic soda.  Plastic compositions, e.g. films, filaments, moulding powders, lacquers, varnishes and coating compositions, comprise a condensation product obtainable as described above and a base material compatible therewith, e.g. a cellulose derivative such as cellulose acetate, nitrate, formate, butyrate or propionate or other cellulose ester, methyl, ethyl or benzyl cellulose or other cellulose ether, or a synthetic resin, e.g. polyvinyl acetate or other polyvinyl compound, with or without volatile solvents, e.g. acetone, other plasticizers, medium or high boiling solvents, natural or synthetic resins, fire retardants and effect materials. The compositions in the form of solutions are useful as adhesives, coating or impregnating compositions, e.g. for the protection of rubber or other insulation or for coating cellulose derivative sheets or surfaces of metal, bricks, cement or plaster, for the manufacture of foils, films or filaments or for mixing with colouring materials to yield inks for printing plastic materials such as cellulose acetate film.  The solid compositions may be moulded, e.g. into rods, tubes or blocks by pressure or injection moulding, or worked up into sheets suitable for use as reinforcing material in splinterless glass.  In examples, coating compositions are prepared by mixing one of the products of the examples above with various proportions of cellulose acetate, triacetin, acetone or methyl ethyl ketone, alcohol, benzene, diacetone alcohol and a pigment or dye. The triacetin may be replaced by dimethyl phthalate, dibutyl tartrate, monomethyl xylene sulphonamide or other plasticizers, the diacetone alcohol by ethyl lactate, cyclohexanone, ethylene glycol monomethyl ether, dioxane or other solvents, and the cellulose acetate by nitrocellulose, benzyl cellulose, ethyl cellulose or polyvinyl acetate.