Poly(hydroxy amide ethers): New high-barrier thermoplastics

The synthesis of a new class of high-barrier polymers, poly(hydroxy amide ethers), is described. The polymers are formed by the reactions of bisphenol-a diglycidyl ether, OCH2CHCH2OC6H4C(CH3)(2)C6H4OCH2CHCH2O, and amide-containing bisphenols of the general formula HOC6H4-NHC(O)RC(O)NHC6H4OH [R = -(CH2)(n)-, -CH2C6H4CH2-, or -C6H4-] or HOC6H4NHC(O)C6H4OH at 140-160 degrees C in propylene glycol monophenyl ether solvent using ethyltriphenylphosphonium acetate as initiator. High-molecular-weight poly(hydroxy amide ethers) of the general structure [-CH2CH(OH)CH2OC6H4C(CH3)(2)C6H4OCH2CH(OH)CH2O C6H4NHC(O)RC(O)NHC6H4O-](n) or [-CH2CH(OH)CH2OC6H4C(CH3)(2)C6H4OCH2CH(OH)CH2OC6H4NHC(O)C6H4O-](n) are readily prepared. The amorphous thermoplastics have glass transition temperatures (T-g) of 90-133 degrees C and oxygen transmission rates (O(2)TR) which range from 0.7 to 4.6 cc . mil/100 in.(2) . atm . day (barrier units or BU) at 23 degrees C and 47-85% relative humidity. The effect that polymer structure has on oxygen barrier properties and T-g is described. The characterization, structure determination, and properties of the poly(hydroxy amide ethers), as well as the amide-containing bisphenol precursors, are also presented.