Patent GB-405797-A (GB)
Title: Improvements in or relating to the preservation of oxidisable organic material such as rubber
IPC: C08K5/3437
Filed: 1933-01-30
Abstract: The oxidation of fatty oils, petroleum oils and soaps is retarded by the addition of a meso-disubstituted acridane.  Simple acridanes having two alkyl groups on the meso carbon atom and no other substituent are preferred, but there may be substituents on both the benzene nuclei, and the benzene groups may be replaced by naphthalene or other condensed ring nuclei substituted or not. The anti-oxidant may be added in the form of a solution or as a dispersion.  Compounds mentioned are meso-dimethyl acridane, meso-methyl ethyl acridane, meso-diethyl acridane, meso-dipropyl acridane, meso-dibutyl acridane, meso-methyl butyl acridane, meso-methyl phenyl acridane, meso-ethyl phenyl acridane, meso-diphenyl acridane, meso-ditolyl acridane, p-p<1> dimethyl meso-dimethyl acridane, p-p<1> di-isopropyl meso-dimethyl acridane, p-p<1> dimethoxy-meso-diphenyl acridane, meso-dimethyl naphthacridane, meso-diphenyl di-naphthacidane.ALSO:The oxidation of oxidizable organic substances such as rubber, fatty oils, petroleum oils and soaps is retarded by the addition to the material of a meso-disubstituted acridane.  The preferred members of the class are the simple acridanes having two alkyl groups on the mesocarbon atom and having no other substituent. However, substituents on both the benzene nuclei, and the replacement of the benzene nuclei by naphthalene and other condensed ring nuclei, substituted or not, is included in the invention.  Compounds mentioned are meso-dimethylacridane, meso-methylethylacridane, meso-diethylacridane, meso-dipropylacridane, meso - dibutylacridane, meso - methylbutyl acridane, meso-methylphenylacridane, meso-ethylphenylacridane, meso - diphenylacridane, meso - ditolylacridane, p - p<1> - dimethyl meso - dimethylacridane, p - p<1> - di - isopropyl meso - dimethylacridane, p - p<1> - dimethoxy meso - diphenylacridane, meso - dimethyl naphthacridane, meso diphenyldi-naphthacridane.  In an example meso-dimethylacridane is prepared by treating the methyl ester of N-phenyl anthranilic acid with magnesium methyl iodide and dehydrating the o-phenylamino phenyl dimethylcarbinol so obtained.ALSO:The oxidation of oxidizable organic substances such as rubber and the like, fatty oils, petroleum oils, soaps, &c., is retarded by the addition to the material of a meso-disubstituted acridane. The preferred members of the class are the simple acridanes having two alkyl groups on the meso carbon atom and having no other substituent.  However substituents on both the benzene nuclei, and the substitution of naphthalene and other condensed ring nuclei substituted or not, for the benzene groups is included in the invention.  The anti-oxidant may be added in the form of a solution or as a dispersion to latex, or painted on the surface of the vulcanized or unvulcanized product, or mixed on the mill with the rubber stock.  The anti-oxidants according to this invention are stated to be applicable to the cold vulcanization, or acid cure process.  Compounds mentioned are meso-dimethyl acridane, meso-methyl ethyl acridane, meso-diethyl acridane, meso-dipropyl acridane, meso-dibutyl acridane, meso-methyl butyl acridane, meso-methyl phenyl acridane, meso-ethyl phenyl acridane, meso-diphenyl acridane, meso-ditolyl acridane, p-p1 dimethyl meso-dimethyl acridane, p-p1 di-isopropyl meso-dimethyl acridane, p-p1 dimethoxy meso-diphenyl acridane, meso-dimethyl naphthacridane, meso-diphenyl dinaphthacridane.  In an example meso-dimethyl acridane is prepared by treating the methyl ester of N-phenyl anthranilic acid with magnesium methyl iodide and dehydrating the O-phenylamino phenyl dimethyl carbinol so obtained.