High-Barrier Poly(hydroxy amide ethers):  Effect of Polymer Structure on Oxygen Transmission Rates. 2

• Published in: Macromolecules 1998-04, Vol.31 (8), p.2622-2630
• Main Authors: Brennan, David J, Haag, Anthony P, White, Jerry E, Brown, Charles N
• Format: Article
• Language: English
• ISSN: 0024-9297; 1520-5835
• DOI: 10.1021/ma971371b

The synthesis of a series of new high-barrier poly(hydroxy amide ethers) is described. The polymers are formed by the reactions of Bisphenol A diglycidyl with a series of N,N‘-alkylenebis(4-hydroxybenzamides) of general formula HOC6H4CONHRNHCOC6H4OH [R = −(CH2)2 - 6−, −CH2CH(OH)CH2−, −CH2C6H4CH2−, or −C6H4−] at 140−160 °C in propylene glycol monophenyl ether solvent using ethyltriphenylphosphonium acetate as initiator. Poly(hydroxy amide ethers) of general structure [−CH2CH(OH)CH2OC6H4C(CH3)2C6H4OCH2CH(OH)CH2OC6H4CONHRNHCOC6H4O−] n are readily prepared in high molecular weight. These amorphous thermoplastics have glass transition temperatures (T g) of 110−152 °C and oxygen transmission rates (O2TR) which range from 1.0 to 2.8 cc·mil/(100 in.·atm·day) (barrier units or BU) at 23 °C and 58−86% relative humidity. The effect that polymer structure has on O2TR and T g is discussed. Of special interest is the poly(hydroxy amide ether) in which R = m-C6H4−. This polymer combines a good oxygen barrier (1.5 BU) with the T g of an engineering thermoplastic (152 °C).