Poly(hydroxy ether sulfonamides). A new class of epoxy‐based thermoplastics

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.

Poly(hydroxyaminoethers): A New Family of Epoxy-Based Thermoplastics

“…[8] Further, although we and others have shown that reactions of ADGE with bisphenols afford a stunning variety of poly(hydroxyethers) (see Sec. 4) comparable in molecular weight to those prepared by the direct sequence of Scheme 1, [9,10] we have found that polymerizations of ADGE with dinucleophilic amines, [11] dicarboxylic acids, [12] dithiols, [6] and disulfonamides [13] often yield polymers with combinations of barrier performance and other properties that cannot be realized with poly(hydroxyethers), at least without resorting to unusual and commercially unavailable bisphenols. [6] Of special interest are poly(hydroxyaminoethers), recently commercialized under the tradename BLOX Adhesive and High-Adhesion Barrier Resins (trademark of the Dow Chemical Company).…”

Semi-Fluorinated Epoxy Thermoplastics Containing the α-Methylstilbene Linkage

“…After 48 h, a slight excess of bisphenol was added to end-cap any remaining epoxide groups. The end-capping reaction was followed by 13 C NMR and the disappearance of the characteristic oxirane carbon signal near 51 ppm confirmed that end-capping was complete (figure 1).…”

“…The resulting polyhydroxyethers form tough, ductile thermoplastics with pendant hydroxyl groups that promote adhesion to or compatibility with polar materials and surfaces. These 'phenoxy-type' thermoplastics are emerging as a new class of high-barrier polymers as well [3][4][5][6][7][8][9][10][11][12][13].…”

High-Barrier Poly(hydroxy amide ethers): Effect of Polymer Structure on Oxygen Transmission Rates. 3

“…60,61 This is reflected by the fact that the barrier properties for poly(hydroxy amide ethers) 23-39 improve (i.e., O 2 TR decreases) as the aromatic core unit (Ar) either (a) becomes less bulky and more compact or (b) contains strong hydrogen bonding groups. 14 In the sections that follow, the 17 poly(hydroxy amide ethers) shown in Table 4 (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39) are compared to one another to show the effects that key structural features have on O 2 TR in the polymers.…”

“…Overall, O 2 TR decreases from 1.8 BU for the hexafluoroisopropylidenebisphenol-based 23 to 0.2 BU for polymer 38, which contains the 2,6-naphthylene unit. O 2 TR decreases incrementally as the Ar unit converts from tetrahedral geometry (23)(24)(25)(26)29) to the more spacially efficient trigonal planer orientation (33) to a geometry where the aromatic rings are joined linearly (34) or are fused together (32,38). A more indepth analysis is described in the sections that follow.…”