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Step‐growth polymerization of bistriazolinediones with 1,1‐diphenylethylene
Author(s) -
Mallakpour Shadpour E.,
Asghari Jila,
Schollmeyer Dieter
Publication year - 1996
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/(sici)1097-0126(199609)41:1<43::aid-pi580>3.0.co;2-h
Subject(s) - adduct , polymerization , copolymer , polymer chemistry , hexane , polymer , chemistry , organic chemistry
The reactions of 4‐ethyl‐1,2,4‐triazoline‐3,5‐dione (ETD) ( 1 ) and 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione (PhTD) ( 2 ) with 1,1‐diphenylethylene (DPE) ( 3 ) were investigated at room temperature. The reactions are very fast and are completed in less than 4 min. These reactions lead to the formation of two 2 : 1 adducts via double Diels–Alder and Diels–Alder‐ene reactions in a ratio of 1.35 : 1. The structure of these adducts where R = Et were determined by X‐ray analysis of a single crystal. These compounds were used as models for the polymerization reactions. The reaction of bistriazolinediones (1,6‐ bis ‐(3,5‐dioxo‐1,2,4‐triazoline‐4‐yl)hexane and bis ‐( p ‐3,5‐dioxo‐1,2,4‐triazoline‐4‐ylphenyl)methane) with ( 3 ) were carried out in dimethylformanide (DMF). The reactions are fast and gave novel copolymers via repetitive double Diels–Alder and Diels–Alderene polyaddition reactions. These polymers have intrinsic viscosities in a range about 0.08 to 0.31 dl g −1 in DMF. Some physical properties and structural characterization of these copolymers have been studied and are reported.