Patent GB-580184-A (GB)
Title: Resinous condensation product and method of making same
IPC: C08G75/16
Filed: 1944-02-17
Abstract: A rubbery product is obtained by mixing one or more saturated organic compounds with one or more organic compounds containing an olefine linkage or a hydroxy, amido, or amino group, each containing two negative constituents which are split off by an alkaline polysulphide to form an organic polysulphide, heating said mixture with an aqueous alkaline polysulphide solution, and separating the rubbery material produced, said saturated organic compound or materials being present in a major proportion in said mixture.  The alkaline polysulphide should preferably have three to five sulphur atoms per molecule. Where an unsaturated compound is used, the molecular ratio of saturated to unsaturated compound should be such that when multiplied by the number of carbon atoms between the negative substituents of the saturated body and the number of carbon atoms between the negative substituents of the unsaturated body is added, the result is between 10 and 500.  The amounts of saturated and unsaturated bodies should also be proportional to their solubilities in the polysulphide solution, and these solubilities may be adjusted by addition of a mutually miscible solvent, e.g. a lower alcohol or ketone. Unsaturated compounds specified are dichloropropylenes, epidichlorhydrins, allylene dichloride, dichloroethylene, butadiene dichloride, the reaction products (diesters) of unsaturated dicarboxylic acids, e.g. fumaric acid, with a monochlorhydrin such as ethylene, propylene, or butylene chlorhydrin, or of an olefine dihalide with the alkali salt of an unsaturated dicarboxylic acid, esters of one or more chlorhydrins with unsaturated chlor acids such as chloracrylic or chlorcrotonic acids, or reaction products of alkene dihalides with alkali salts of unsaturated halogen acids. Saturated compounds specified are olefine dihalides, e.g. ethylene, propylene, or butylene chloride or bromide, b b 1-dichlorodiethylether, the esters from a halogen hydrin and a halogen-substituted acid or acid halide, the amide from an aliphatic or aromatic diamine and an aliphatic monocarboxylic chlor-acid, the diester from an olefine dihalide and a disodium salt of a saturated dicarboxylic acid, e.g. succinic, adipic, or sebacic acids, or the reaction product of an olefine dihalide or dichloroether with a sodium salt of a saturated halogen-substituted monocarboxylic acid, e.g. chloracetic or chlorbutyric acids.  Hydroxy, amido, or amino compounds specified are 2.4-dichloroaniline, 2.4-dibromaniline, a b -glycerol dichlorhydrin, glycerol dichloroacetate, dichloracetamide, and diesters of ethylene chlorhydrin with hydroxyphthalic acid. Vulcanizing agents employed when unsaturated compounds are used are sulphur and selenium, and when hydroxy, amido or amino bodies are employed, polycarboxylic acids or anhydrides (e.g. phthalic, sebacic), polyisocyanates, or a rubbery product containing free carboxylic groups.  The polysulphide may be prepared by boiling a slurry of lime or alkali metal hydroxide with sulphur or by fusing sulphur with sodium disulphide.  The products are masticated with carbon black vulcanizing agents such as zinc oxide, an organic accelerator and any additional sulphur.  In example (1), aqueous sodium polysulphide is mixed and heated with ethyl alcohol, ethylene dichloride and butadiene dichloride, and the product is compounded and cured with carbon black, zinc oxide, sulphur, stearic acid and benzothiazyldisulphide.  The butadiene dichloride may be replaced by a dichloroamine, e.g. dichloroaniline, or a hydroxy-alkylene dichloride, e.g. glycerol dichlorhydrin, in which case a polycarboxylic acid or anhydride is used for vulcanization.  In example (2), a mixture of 2.21-dichloroethylesters, prepared from a mixture of succinyl chloride with either fumaryl or maleyl chloride and ethylene chlorohydrin, is warmed with calcium polysulphide, and the product is compounded and cured as in example (1).  If freshly precipitated magnesium hydroxide, barium sulphate, or a dispersing agent is present in the polysulphide solution, the product is obtained as a latex.