Crosslinking of poly(arylene disulfide)s and poly(arylene sulfane)s derived from cyclic(arylene disulfide) oligomers

Abstract

Cyclic(arylene disulfide) and polycyclic(arylene sulfide) oligomers were synthesized by catalytic oxidation of arylenedithiols or arylenetritthiols with oxygen in the presence of a copper-amine catalyst. These cyclic(arylene sulfide) oligomers can undergo free radical ring-opening polymerization at an elevated temperature in the melt or solution. Polycyclic(arylene sulfide) oligomers can be used to crosslink poly(arylene disulfide)s and poly(arylene sulfane)s derived from cyclic(arylene disulfide) oligomers and elemental sulfur. The crosslinking reactions were investigated by differential scanning calorimetry and by solubility of the cured products. The minimum concentrations of polycyclic(arylene sulfide) oligomers for producing a well crosslinked poly(arylene disulfide) and poly(aryelene sulfane) are 7 wt% and 10 wt%, respectively. The crosslinking reactions between poly(arylene disulfide)s, poly(arylene sulfane)s, and triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (TTT) were also investigated. TTT is more efficient for crosslinking than the synthesized polycyclic(arylene disulfide) oligomers. The crosslinkable poly(arylene disulfide)s and poly)arylene sulfane)s could be potentially used as high temperature coatings, sealants, adhesives, and as matrices for high performance thermoset composites.