Synthesis and properties of some new polyimidosulfides with highly mobile backbones

Abstract

Various alkanedithiols [HSRSH; R = (CH2)3–6 orCH2CH2OCH2CH2] add to the carbon‐carbon double bonds of N,N′‐bismaleimido‐1,8‐octane (1) at room temperature in m‐cresol that contains triethylamine as a catalyst to produce the corresponding polyimidosulfides (3) in yields of 75–86% and with inherent viscosities (ηinh) of 0.30–1.05 dL/g. In general (3) are amorphous, elastomeric materials that undergo glass transitions (Tg) within the range of 6.5–13°C but product (3a) [R = (CH2)6] is a tough, leatherlike polymer that exhibits Tg = 35°C and a melting transition at 77°C. X‐ray analysis indicates that (3a) is ca. 37% crystalline. In addition to further details of the synthesis and properties of polyimidosulfides (3), comparisons are made between crystalline (3a) and a structurally analogous but morphologically dissimilar, elastomeric polyaspartimide synthesized earlier from (1) and N,N′‐dimethyl‐1,6‐hexanediamine.

Chemistry and properties of addition polyimides

“…Bismaleimides and bisnucleophiles have been exploited in syntheses of a variety of linear polymers. Dithiols [57][58][59][60][61] and diamines [62][63][64][65] are the favoured bisnucleophiles because of their high basicity.…”

Synthesis and properties of bismaleimide resins containing ether bonds

“…Bismaleimides were prepared from corresponding diamines and maleic anhydride by a modification of the method of White et al 5 General procedure for the preparation of bismaleimides are as follows. A 1000-mL four-necked flask was charged with maleic anhydride (1.10 mol) and dry acetone (200 mL).…”

Studies on interpentrating polymer networks of polyurethane and polybismaleimide. I. Polyurethane and bismaleimide-urethane copolymer

“…There is no evolution of small molecules during its polymerization [2][3][4][5]. The cured resin has excellent thermal stability.…”