It was found that 1, 3-dipolar addition to double bond is available for vulcanization of rubber. For example, terephthal-aldehyde (3.12phr) and phenyl hydroxylamine (5.07phr), whose molar ratio is 1:2, are capable of vulcanzing polybutadiene, SBR, Diene rubber and nitrile rubber at 150°C for 30 minuites to yield vulcanizates. Cross-linking efficiency was found to be 0.06-0.08 mole linking per mole of aldehydes. Carbon black ingredient is an efficient filler but it retards vulcanization. The reason for the retardation is elucidated by the experiment of addition towards styrene to be due to quinone group located on carbon black surface, because both carbon black and quinone retards the addition to styrene. This undesirable property is much improved by use of excess amount of terephthalaldehyde (8.3phr) and phenyl hydroxylamine (6.75phr), whose molar ratio is 1:1, and in this way a vulcanizate of high tensile property, 170kg/cm
2 in tensile strength, 470% in elongation, is prepared.
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