GB570232A - Improvements in anti-oxidants - Google Patents

Abstract

Antioxidants for rubber, balata, guttapercha, &c. or synthetic rubber, unsaturated vegetable or other fatty oils, essential oils, petroleum oils and their derivatives, gasoline, soaps, aldehydes, synthetic resins, turpentine or paints, &c., comprise the reaction products of an olefine oxide with an aromatic di-secondary amine. The oxide may be ethylene-, propylene-, butylene-, amylene- or tri-, tetra- or pentamethylene oxide, and the amine may have the formula R1-NH-Ar-NH-R2, where Ar is an arylene group, and R1 and R2 are each aromatic groups such as phenyl, naphthyl, &c. which may include further substituents, e.g. diphenyl, ditolyl-, dianisyl-, dinapthyl, dihydro-phenyl-, or dixylyl phenylene diamine, diphenyl p-tolylene diamine, diphenyl naphthalene diamine diamino-diphenyl. The oxide or vapour may be passed through the amine, or a solution of the reactants in dioxane or benzene may be refluxed, or the reactants may be heated in a sealed tube. A halogen or halogen acid &c. catalyst may be used. If acid, the products may be neutralized with alkali. In an example, 6 c.c. of ethylene oxide were reacted with 26 gms. of N,N1-diphenyl p-phenylene diamine by heating overnight at 175 DEG C. and 1 per cent of the purified product, a thick oil, added to smoked sheet rubber in a mix including carbon black, zinc soap, pine tar, zinc oxide, sulphur and an accelerator.ALSO:Antioxidants for rubber, balata, guttapercha, &c. or synthetic rubber, unsaturated vegetable or other fatty oils, essential oils, petroleum oils and their derivatives gasoline, soaps, aldehydes, synthetic resins, turpentine or paints, &c., comprise the reaction products of an olefine oxide with an aromatic di-secondary amine. The oxide may be ethylene-, propylene-, butylene-, amylene- or tri-, tetra- or pentamethylene oxide, and the amine may have the formula R1-NH-Ar-NH-R2, where Ar is an arylene group, and R1 and R2 are each aromatic groups such as phenyl, naphthyl, &c. which may include further substituents, e.g. diphenyl, ditolyl-, dianisyl-, dinaphthyl-dihydroxy phenyl-, or dixenyl phenylene diamine, diphenyl p-tolylene diamine, diphenyl naphthalene diamine, or dianilino diphenyl. The oxide or vapour may be passed through the amine, or a solution of the reactants in dioxane or benzene may be refluxed, or the reactants may be heated in a sealed tube. A halogen or halogen acid &c. catalyst may be used. If acid, the products may be neutralized with alkali. In an example, 6 c.c. of ethylene oxide were reacted with 26 gms. of N,N1 - diphenyl p-phenylene diamine by heating overnight at 175 DEG C. and 1 per cent of the purified product, a thick oil, added to smoked sheet rubber in a mix including carbon black, zinc soap, pine tar, zinc oxide, sulphur and an accelerator.