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Synthesis of a Liquid Bisoxazolin‐5‐one by Radical Reaction of Bismercaptan onto 2‐Ethenyloxazolin‐ 5‐one
Author(s) -
SaintLoup René,
Robin JeanJacques,
Boutevin Bernard
Publication year - 2002
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/1521-3935(20020101)203:1<199::aid-macp199>3.0.co;2-l
Subject(s) - chemistry , ether , side chain , polymer chemistry , ring (chemistry) , thermal stability , coupling reaction , organic chemistry , catalysis , polymer
The synthesis of a liquid chain‐coupling agent obtained by the radical diaddition of bis(mercaptoethyl) ether on 2‐ethenyl‐4,4‐dimethyloxazolin‐5‐one is described. Different methods of synthesis have been studied and their products were characterized by IR, 1 H NMR spectroscopy, and by SEC. The classic thermal radical initiation leads to bisazlactone compounds, but a side reaction of azlactone ring opening occurs, which prevents this product from being employed as a chain‐extender. The low thermal initiation and the UV initiation lead to interesting products, but they are not suitable for being employed as chain‐coupling agent because of their functionality (less or more a difunctional compound). The most interesting method consists in synthesizing by low thermal initiation in a first step, and then in transforming residual 2‐ethenyl‐4,4‐dimethyloxazolin‐5‐one by UV initiation in a second step. The compound is composed by more than 95 per cent of difunctional azlactone compound and a few polyazlactone functional compound. The final compound is a stable liquid at room temperature under nitrogen atmosphere.