Amine‐induced copolyaddition of p‐chlorophenyl glycidyl ether with cis‐hexahydrophthalic anhydride

The copolyaddition reaction ofp‐chlorophenyl glycidyl ether with cis‐hexahydrophthalic anhydride was investigated in the presence of tri‐n‐butylamine in xylene by varying monomer compositions. The yield and the molecular weight of the polymeric product increased with time and had maximum values at the equimolar mixture of monomers. The amine is found to suppress largely the undesirable side reactions of epoxide and anhydride homopolymerizations. With excess epoxide, the copolymers are better than 90% hydroxylterminated, and with a large excess of anhydride, carboxyl termination predominates. Agreement between the partial epoxide contents without chain end units in polymeric products by the chlorine content and by the saponification number is very good to about 50 mole‐%, which implies that both epoxide and anhydride become strictly bifunctional toward each other. The suitability of the mechanism proposed previously for this reaction was discussed in the light of the observed phenomena.