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Polymerization of Triazolinediones with trans ‐3,3‐Dichloro‐1‐phenyl‐1‐propene
Author(s) -
Mallakpour Shadpour E.,
Mohammdi Farhad,
Kolshorn Heinz
Publication year - 1997
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(199703)42:3<328::aid-pi725>3.0.co;2-z
Subject(s) - propene , polymerization , methylene , ene reaction , chemistry , yield (engineering) , diels–alder reaction , dimethylformamide , polymer chemistry , polymer , proton nmr , carbon 13 nmr , organic chemistry , materials science , catalysis , solvent , metallurgy
The reaction of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione (PhTD) ( 2 ) with trans ‐3,3‐dichloro‐1‐phenyl‐1‐propene ( 4 ) was investigated at room and reflux temperatures in methylene chloride solution. Although the reaction is slow, it gives quantitative yield. This reaction leads to the formation of two 2:1 adducts via double Diels–Alder and Diels–Alder‐Ene reactions in a ratio of about 1: 7. The major product was isolated by means of fractional crystallization as a pure compound and was characterized by infra‐red (IR), 1 H nuclear magnetic resonance (NMR), 13 C NMR, mass spectra and elemental analysis. The structure of the minor product was determined by IR and 1 H NMR. 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 ( 4 ) was carried out in dimethylformamide (DMF). The reactions gave novel polymers via repetitive double Diels–Alder and Diels–Alder‐Ene polyaddition reactions, with the major component being a Diels–Alder‐Ene structure. These polymers have intrinsic viscosities in a range from 0·08 to 0·18dlg ‐1 in DMF. The physical properties and structural characterization of these polymers have been studied and are reported. © of SCI.