Synthesis of poly(cyanurate)s by a novel polyaddition of bis(epoxide)s with triazine dichloride

Poly(cyanurate)s (P‐1–P‐4) containing triazine groups in the main chain and pendant chloromethyl groups in the side chain were synthesized by the polyaddition of bis(epoxide)s with 2,4‐dichloro‐6‐(diphenylamino)‐s‐triazine (DPAT) using quaternary onium salts as catalysts. The polyaddition of diglycidyl ether of bisphenol‐A (DGEBA) with DPAT proceeded smoothly in chlorobenzene at 100 °C for 12 h to give P‐1 with M_n = 19,000 in a 92% yield, when tetrabutylammonium chloride (TBAC) was used as a catalyst. However, no reaction occurred without a catalyst or with triethylamine alone under the same reaction conditions. Polyadditions of other bis(epoxide)s with DPTA also proceeded smoothly using 5 mol % of TBAC as a catalyst in chlorobenzene to produce corresponding polymers (P‐2≈P‐4) in high yields under similar reaction conditions. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 4006–4012, 2000