Anti-degradant efficiency of benzylamino derivatives as non-staining anti-ozonant and aminomethylphenol derivatives as anti-ozonant and anti-oxidant was estimated by the priventive rate of viscocity decrease of polyisoprene-chloroform solution and ozone cracking resistance effect on SBR compounds.
The results were obtained that substituted benzylamino derivatives that contained the N atom on substituent had remarkable anti-ozonant efficiency, and its efficiency was elevated by increasing the N atom on substituent.
Besides, anti-ozonant efficiency of aminomethylphenol derivatives gave the following results (1)-(3).
(1)
p-Aminomethylphenol was more effective than o-aminomethylphenol.
(2) The efficiency was elevated as increasing the number of aminomethyl group.
(3) The order of the efficiency of aminomethyl group was -NMe<-NEt<-NC
3H
6OMe<-NC
3H
6 NMe, and it was found that the N atom on substituent was effective to reaction with ozone.
Anti-oxidant efficiency of aminomethylphenol was effective only p-aminomethylphenol. As
o-aminomethylphenol formed the intramoleculer hydrogen bond of six membered ring, it seemed that the OH group and
N atom were deactivated.
In order to clarify the reaction mechanism of
N-substituted alkyl group with ozone,
N, N-dimethylbenzylamine was used as model compound, and the reaction products were isolated and identified. It was found that the main products of ozonisation were
N-methyl-
N-benzylformamide and benzaldehyde.
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