Patent GB-714072-A (GB)
Title: Rubber antioxidants and their application
Inventor: JACKSON HARRY EDWARD
IPC: C08K5/138
Filed: 1951-07-16
Abstract: The deterioration by oxidation of synthetic rubbers, e.g neoprene, is prevented by adding before vulcanization a normal or basic salt of aluminium, barium, calcium, magnesium, strontium or zinc of a , a -bis-(2-hydroxy-3:5-dialkyl-phenyl) alkane. Specified salts are those of the above-mentioned metals with the following compounds: bis-(2-hydroxy-3:5-dimethyl phenyl) methane, bis-(2-hydroxy-5-methyl-3-tert-butyl phenyl) methane, bis-(2-hydroxy-5-methyl-3-tert-amyl phenyl) methane, a , a -bis-(2-hydroxy-3:5-dimethyl phenyl) ethane, a , a -bis-(2-hydroxy-3:5-dimethyl phenyl) propane, a , a -bis-(2-hydroxy-3:5-dimethyl phenyl) butane, a , a -bis-(2-hydroxy-3:5-dimethyl phenyl iso butane, a , a -bis-(2-hydroxy-3:5-dimethyl phenyl) heptane, a , a -bis-(2-hydroxy-5-methyl-3-octyl phenyl) butane, a , a -bis-(2-hydroxy-5-methyl-3-tert-butyl phenyl) butane, a , a -bis-(2-hydroxy-3:5-dioctyl phenyl) butane, a , a -bis-(2-hydroxy-3:5-dimethyl phenyl) nonane, a , a -bis-(2-hydroxy-3-methyl-5-ethyl phenyl) nonane, a , a -bis-(2-hydroxy-3:5-dimethyl phenyl) octane, a , a -bis-(2-hydroxy-3:5-dimethyl phenyl) dodecane, a , a -bis-(2-hydroxy-3:5-dimethyl phenyl) d , e , e -trimethylhexane. In an example, the antioxidant effect is shown upon a mix consisting of neoprene, light calcined magnesia, stearic acid, china clay, whiting, petroleum jelly, pale cumar resin, titanium dioxide and zinc oxide. Specifications 525,737 and 651,369, [Group IV (b)], are referred to.ALSO:Normal and basic aluminium, barium, calcium, magnesium, strontium, and zinc salts of a  : a  - bis - (2 - hydroxy - 3 : 5 - dialkylphenyl)-alkanes, which may be used as antioxidants for rubber (see Groups IV (a) and V) are prepared by the condensation of appropriate 2 : 4-dialkyl-phenols and saturated aliphatic aldehydes in the presence of acid condensing agents followed by the conversion of the resulting a  : a -bis-(2-hydroxy-3 : 5-dialkylphenyl)-alkanes to the normal and basic salts of the above-mentioned metals. Specified salts are those of the above-mentioned metals with the following compounds: bis-(2-hydroxy-3 : 5 - dimethylphenyl) - methane, bis - (2-hydroxy - 5 - methyl - 3 - tert - butylphenyl)-methane, bis - (2 - hydroxy - 5 - methyl - 3-tert - amylphenyl) - methane, a  : a  - bis - (2-hydroxy - 3 : 5 - dimethylphenyl) - ethane, a  : a  - bis - (2 - hydroxy - 3 : 5 - dimethylphenyl) - propane, a  : a  - bis - (2 - hydroxy-3 : 5 - dimethylphenyl) - butane, a  : a  - bis-(2 - hydroxy - 3 : 5 - dimethylphenyl) - iso-butane, a  : a  - bis - (2 - hydroxy - 3 : 5 - dimethylphenyl) - heptane, a  : a  - bis - (2-hydroxy - 5 - methyl - 3 - octylphenyl) - butane, a  : a  - bis - (2 - hydroxy - 5 - methyl - 3 - tert-butylphenyl) - butane, a  : a  - bis - (2 - hydroxy-3 : 5 - dioctylphenyl) - butane, a  : a  - bis - (2-hydroxy - 3 : 5 - dimethylphenyl) - nonane, a  : a  - bis - (2 - hydroxy - 3 - methyl - 5 - ethylphenyl) - nonane, a  : a  - bis - (2 - hydroxy-3 : 5 - dimethylphenyl) - octane, a  : a  - bis-(2 - hydroxy - 3 : 5 - dimethylphenyl) - dodecane, a  : a  - bis - (2 - hydroxy - 3 : 5 - dimethylphenyl) - a  : e : e  - trimethylhexane. Specifications 525,737 and 651,369 are referred to.ALSO:The deterioration by oxidation of natural and synthetic rubbers may be prevented by adding before vulcanization a normal or basic salt of aluminium, barium, calcium, magnesium, strontium or zinc of a a -bis-(2 hydroxy-3:5-dialkyl-phenyl) alkane.  These salts may be made by condensing the appropriate 2:4 dialkyl phenols with saturated aliphatic aldehydes and then precipitating the appropriate salt from the resulting a a -bis-(2-hydroxy-3:5-dialkyl phenyl) alkane as described in Group IV (b).  Specified salts are those of the above-mentioned metals with the following compounds:-bis-(2-hydroxy-3:5-dimethyl phenyl) methane, bis-(2-hydroxy-5-methyl-3-tert-butyl phenyl) methane, bis-(2-hydroxy-5-methyl-3-tert-amyl phenyl) methane. a a -bis-(2-hydroxy-3:5-dimethyl phenyl) ethane, a a -bis-(2-hydroxy-3:5-dimethyl phenyl) propane, a a -bis-(2-hydroxy-3:5-dimethyl phenyl) butane, a a -bis-(2-hydroxy-3:5-dimethyl phenyl) iso butane, a a -bis-(2-hydroxy-3:5-dimethyl phenyl) heptane, a a -bis-(2-hydroxy-5-methyl-3-octyl phenyl) butane, a a -bis-(2-hydroxy-5-methyl-3-tert-butyl phenyl) butane, a a -bis-(2-hydroxy-3:5-dioctyl phenyl) butane, a a -bis-(2-hydroxy-3:5-dimethyl phenyl) nonane, a a -bis-(2-hydroxy-3-methyl-5-ethyl phenyl) nonane a a -bis-(2-hydroxy-3:5-dimethyl phenyl) octane, a a -bis-(2-hydroxy-3:5-dimethyl phenyl) dodecane, a a -bis-(2-hydroxy-3:5-dimethyl phenyl) g e e  trimethylhexane.  In examples, the antioxidant effect of many alkane salts of the invention is shown upon mixes consisting of pale crepe rubber, zinc oxide, blanc fixe, stearic acid, titanium dioxide, sulphur, and diphenylamine or zinc diethyldithiocarbamate or tetramethylthiuram monosulphide; or upon guttapercha. Specifications 525,737 and 651,369 are referred to.