Modification of diene polymers and polymer synthesis by reaction of triazolinediones with olefinic bonds

Abstract

Triazolinediones are exceptionally strong electron acceptors and are among the most powerful reagents known for unconjugated CC bonds. They react with vinyl ethers and esters, styrenes, β-diketones and allylic compounds to form novel copolymers. However, the main objective of this report is to review the use of triazolinediones as low temperature modifiers for diene polymers and to report on their influence on polymer properties. This reaction is exceptionally versatile since the number of unsaturated bonds reacting is proportional to the quantity of triazolinedione. Depending on the degree of modification, the polymers formed range from thermoplastic elastomers to rigid amorphous polymers with high softening points. The modified polymers have much higher glass and softening points, become increasingly soluble in polar solvents with increasing conversion, possess remarkably acidic protons and show substantial decreases in molecular size. Poly-1,2-butadiene, 5% modified, had elongation to break, Young's modulus and tensile strength double that of the unmodified material also tensile recoveries were >90%. Bis-triazolinediones are effective cross-linking agents at room temperature.