On exposure to sterilizing doses of Co-60 gamma-rays, bisphenol-A poiy
carbonate (BPA-PC) turns a moderately intense yellow color. Product st
udies of gamma-ray irradiated BPA-PC and a model compound, BPA-PC cycl
ic tetramer, were undertaken to define the major degradative process i
nvolved, and to try to identify the chemical species responsible for t
he color. The major irradiation products were isolated and identified
using base hydrolysis followed by HPLC/MS analysis. These studies show
that the principal degradative process induced by gamma-ray irradiati
on involves Fries type free radical reactions leading to the destructi
on of the carbonate linkages and formation of a number of phenol coupl
ing products and salicylate esters. Chromatographic/spectroscopic stud
ies indicated that the yellow color was mainly due to the formation of
two labile products having a broad lambda(max) at similar to 360 nm.
However, numerous attempts to isolate and identify these compounds usi
ng HPLC/MS and GC/MS were unsuccessful.