Patent GB-919711-A (GB)
Title: Improvements relating to the oxidative stabilisation of sensitive organic substancesand products stabilised from oxidative deterioration
IPC: C08G69/02
Filed: 1960-04-19
Abstract: Hydrocarbons, especially mineral oils such as benzine; waxes; and animal and vegetable oils such as cottonseed oil are stabilized against oxidative deterioration by the incorporation therein of 0,001-5% by weight of a compound of general formula <FORM:0919711/III/1> or a salt thereof with an organic non-aromatic carboxylic acid, wherein n is 1 or 2, A is an n-valent isocyclic or heterocyclic aromatic radical, B is a saturated aliphatic radical of at least 3 carbon atoms which is bound to the N atoms by means of C atoms in the a  and g  positions, preferably the propane radical E -CH2-CH2-CH2-, and either R1 is hydrogen and R2 is hydrogen or an acyl group, or R1 and R2 together form a bivalent alkylidene or arylalkylidene group.  If required, R2 may be a divalent acyl radical derived from a dicarboxylic acid and may be bound to a second residue of the above general formula.  It is preferred to use N-(p-hydroxyphenyl)- and N-(p-aminophenyl)- 1 :3-diaminopropanes for benzines and other mineral oils.ALSO:Rubber, synthetic elastomers, and polyolefins such as polyethylene are stabilized against oxidative deterioration by the incorporation therein of 0,001-5% by weight of a compound of general formula <FORM:0919711/IV(a)/1> or a salt thereof with an organic non-aromatic carboxylic acid, wherein n is 1 or 2, A is an n-valent isocyclic or heterocyclic aromatic radical, B is a saturated aliphatic radical of at least 3 carbon atoms which is bound to the N atoms by means of C atoms in the a  and g  positions, preferably the propane radical -CH2-CH2-CH2-, and either R1 is hydrogen and R2 is hydrogen or an acyl group, or R1 and R2 together form a bivalent alkylidene or arylalkylidene group.  If required, R2 may be a divalent acyl radical derived from a dicarboxylic acid, and may be bound to a second residue of the above general formula.  It is preferred to use N-b -naphthyl-1:3-diaminopropanes for rubber and synthetic elastomers.  A stabilized rubber composition comprises 100 parts latex crepe, 1,5 parts stearic acid, 5 parts zinc oxide, 1 part diphenylguanidine, 2,5 parts sulphur and 1 part of the antioxidant, the composition being vulcanized for 60 mins. at 140 DEG -145 DEG C.ALSO:Enanthol (i.e. hexanol), tetrahydronaphthalene, synthetic ester oils and waxes, and compounds containing ether, aldehyde and unsaturated organic groups or tertiary carbon atoms are stabilized against oxidative deterioration by the incorporation therein of 0.001-5% by weight of a compound of general formula <FORM:0919711/IV (b)/1> or a salt thereof with an organic non-aromatic carboxylic acid, wherein n is 1 or 2, A is an n-valent isocyclic or heterocyclic aromatic radical, B is a saturated aliphatic radical of at least 3 carbon atoms which is bound to the N atoms by means of C atoms in the a  and g  positions, preferably the propane radical -CH2-CH2-CH2-, and either R1 is hydrogen and R2 is hydrogen or an acyl group, or R1 and R2 together form a bivalent alkylidene or arylalkylidene group. If required, R2 may be a divalent acyl radical derived from a dicarboxylic acid and may be bound to a second residue of the above general formula.  It is preferred to use N-phenyl- and N-(p-methoxyphenyl)- 1:3-diaminopropanes for aldehydes and easily polymerizable monomers.  N-aryl-2-hydroxy-1 : 3-diaminopropanes are obtained by reacting an arylamine with epichlorhydrin and then treating the N-(3-chloro-2-hydroxypropyl)-arylamine so obtained with ammonia under pressure.  N-aryl-1 : 3-diaminopropanes are obtained (a) by reacting an arylamine with acrylonitrile and then reducing the N-cyanoethyl arylamine so produced; (b) by condensing 1-bromo-3-amino-propane in the form of its hydrobromide with an arylamine; and (c) by condensing a phenol with 1 : 3-diaminopropane. N-naphthyl-1 : 3-diaminopropanes are obtained by condensing the appropriate naphthol with 1 : 3-diaminopropane in the presence of metaboric acid.