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)2C6H4OCH2CHCH2O, and amide-containing bisphenols of the general formula HOC6H4NHC(O)RC(O)NHC6H4OH [R = −(CH2) n −, −CH2C6H4CH2−, or −C6H4−] or HOC6H4NHC(O)C6H4OH at 140−160 °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)2C6H4OCH2CH(OH)CH2OC6H4NHC(O)RC(O)NHC6H4O−] n or [−CH2CH(OH)CH2OC6H4C(CH3)2C6H4OCH2CH(OH)CH2OC6H4NHC(O)C6H4O−] n are readily prepared. The amorphous thermoplastics have glass transition temperatures (T g) of 90−133 °C and oxygen transmission rates (O2TR) which range from 0.7 to 4.6 cc·mil/100 in.2·atm·day (barrier units or BU) at 23 °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.

No abstract

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).

No abstract

No abstract

No abstract

SYNOPSISBase-initiated polymerizations of N,N'-dimethyl-1,3-benzenedisulfonamide or other N,N'-dialkyldisulfonamides with various arylene-diglycidyl ethers afford a broad range of poly(hydroxy ether sulfonamides) (2). Polymers 2, which represent a new family of epoxy-based thermoplastics, are moldable, amorphous materials characterized by moderate T, "C) and by good barrier t o oxygen, reflected by oxygen transmission rates of 0.45-2.89 cc-mi1/100 in2-atm (0,)-day a t 234 "C and about 60% relative humidity. In addition to a discussion of how structural changes in the backbones of 2 influence their barrier properties, details of the synthesis, thermal analysis and mechanical evaluation of'the polymers are described. 0 1996 J o h n Wiley 8r Sons, Inc.

Oxo‐Verbindungen (I) reagieren mit den Anionen von Acetonitril in (II) über die Addukte (III) zu den substituierten Acetonitrilen (IV).