CPPD
is used as an antioxidant and antiozonant for
natural and synthetic elastomers, as a stabilizer
of polymers and as a monomer polymerization inhibitor. CPPD is not regulated for use in food contact
applications. 6PPD imparts high temperature stability, high
strength, and chemical and electrical resistance.
Antioxidant is a substance added in small quantities to hydrocarbons which are
susceptible to oxidation, such as rubbers, plastics, foods, and oils to inhibit
or slow oxidative processes, while being itself oxidized. Antioxidants work in
two different ways. In primary antioxidants (also called free-radical
scavengers), antioxidative activity is implemented by the donation of an
electron or hydrogen atom to a radical derivative. These antioxidants are
usually hindered amines (p-Phenylene diamine, trimethyl dihydroquinolines,
alkylated diphenyl amines) or substituted phenolic compounds with one or more
bulky functional groups such as a tertiary butyl at 2,6 position commonly.
Butylated hydroxytoluene (BHT) is a common example of hindered phenolic
antioxidant. The reaction order in SN1 mechanism is 3° > 2° > 1° > CH3
(no SN1) so, tertiary butyl groups are substituted in phenolic antioxidant
compounds. Primary antioxidants are free radical scavengers which combine with
peroxy radicals and break autocatalytic cycle. In secondary antioxidants ( also
called peroxide decomposers), activity is implemented by the removal of an
oxidative catalyst and the consequent prevention of the initiation of oxidation.
Examples of peroxide decomposer type of antioxidant are trivalent phosphorous
and divalent sulfurcontaining compound such as sulfides, thiodipropionates and
organophosphites. Synergistic effect is expected when primary antioxidants are
used together with secondary antioxidants as primary antioxidants are not very
effective against the degradation by UV oxidation. Sometimes, chelating agents
are added to scavenge metal impurities which can initiate decomposition.
p-Phenylenediamine is
used as a parent compound in vulcanization accelerators and in antioxidants for rubber
industry. PPD is chosen because it imparts high temperature stability, high
strength, and chemical and electrical resistance. Examples of the most widely used anitioxidants or antiozonants derived form
p-phenylenediamine are N-isopropyl-N'-phenyl-p- phenylenediamine (IPPD, CAS #
101-72-4) , N-cyclohexyl-N'-phenyl-p- phenylenediamine (CPPD, CAS #: 101-87-1),
N,N'-Diphenyl-p-henylenediamine (DPPD, CAS # 74-31-7), and N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine
(6PPD, CAS #: 793-24-8). These derivatives are
added to rubber products to retard degradation by oxidants and ozone.
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