Mechanism of Antiozonant Action. II. Effect of Antiozonants on the Ozonization of 2,6-Dimethyl-2,6-Octadiene and 2-Butene

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Abstract
The ozonolysis of 2,6-dimethyl-2,6-octadiene and 2-butene as model compounds for polyisoprene and polybutadiene was investigated using gas chromatography to follow the reaction. Ozonolysis led to mixtures containing mainly the corresponding carbonyl compounds and peroxy compounds, such as ozonides and polymeric peroxides. Ozonization of the model compounds in the presence of antiozonants or addition of antiozonants to the ozonized model compounds indicated that antiozonants react at least in three different ways: (a) All effective antiozonants reacted rapidy with ozone. (b) All antiozonants reacted readily with ozonides and slowly with polymeric peroxides, whereby the corresponding carbonyl compounds were formed. (c) Difunctional secondary amines, such as p-phenylenediamines, reacted readily with the formed aldehydes leading to polymeric compounds. In ozonized polydiene vulcanizates, a relinking of severed chain ends is achieved by this reaction, whereby the diamine becomes attached to the rubber network. Relatively basic amines effect aldol condensation of aldehydes.

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