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Use of controlled radical polymerization of butadiene with AIBN and TEMPO for the determination of the NMR characteristics of hydroxymethyl groups
Author(s) -
Pradel JeanLaurent,
Ameduri Bruno,
Boutevin Bernard
Publication year - 1999
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/(sici)1521-3935(19991001)200:10<2304::aid-macp2304>3.0.co;2-6
Subject(s) - chemistry , polymerization , hydroxymethyl , polybutadiene , radical polymerization , polymer chemistry , bulk polymerization , proton nmr , organic chemistry , copolymer , polymer
The controlled radical polymerization of butadiene initiated with 2,2′‐azoisobutyronitrile (AIBN) and in the presence of 2,2,6,6‐tetramethylpiperidine‐ N ‐oxyl (TEMPO) is presented. The produced oligomers which have number average degrees of polymerization ranging between 3 and 12 were characterized by NMR. This led to the determination of both the end‐groups and the functionality. The hydrolysis of these oligomers yields α ‐hydroxy‐ ω ‐cyano‐polybutadiene. 13 C and 1 H NMR spectra of these products exhibit two characteristic signals of hydroxymethyl groups. The mechanism of the polymerization allows the assignments to cis ‐ and trans ‐CH 2 CH=CH—CH 2 OH groups. In fact, this method also shows that geraniol end‐groups are negligible in commercially available products obtained by the polymerization initiated with hydrogen peroxide.