A series of copolymers are synthesized by repetitive Diels-Alder polyaddition reaction of bifunctional cyclohepta-1,3,5-trienes with bifunctional 1,2,4-triazoline-3,5-diones. The copolymers of different bistriazolinediones with a bisdiene, or of different biscycloheptatrienes with a dienophile, have good solubility in CH2Cl2 and CHCl3, while the homopolymers are poorly soluble. The copolymers were characterized by standard analytical techniques to test the structural regularity of these systems. Due to the kinetic control, it is possible to apply copolymerization statistics to these systems. Based on a model study, it is concluded that alipatic and aromatic bistriazolinediones have the same…

Synthesis of new polymers via Diels–Alder reaction. III. Biscyclohexadienephthalimides as dienes

Difunctional cyclohexadienes with dihydrophthalimide central unitsand phenyl side groups to increase solubility are used as bisdienes in repetitive Diels-Alder polyadditions with bis(4-(1,2,4,-triazoline-3,5-dione-4-yl)phenyl)methane as a difunctional dienophile. The polymers show good solubility in CH 2 Cl 2 and CHCl 3 . Non-stoichiometric Diels-Alder polyaddition with slight excess of the bistriazolinedione provides the possibility of synthesizing telechelics with highly reactive triazolinedione end groups