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Polymerization of 2‐allyl‐1‐methylenecyclohexane by the cyclic polymerization mechanism
Author(s) -
Butler George B.,
Miles Marion L.
Publication year - 1966
Publication title -
polymer engineering and science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.503
H-Index - 111
eISSN - 1548-2634
pISSN - 0032-3888
DOI - 10.1002/pen.760060113
Subject(s) - cationic polymerization , polymerization , monomer , polymer chemistry , chain growth polymerization , materials science , polymer , chemistry , radical polymerization , organic chemistry
2‐Ally‐1‐methylenecyclohexane is a compound which is functionally capable of undergoing polymerization by the alternating intra‐intermolecular propagation mechanism to produce poly[1,8‐methylene[4.3.0] bicyclononane]. This monomer was synthesized and its polymerization through use of cationic and Ziegler‐type initiators was studied. Synthesis of the monomer was accomplished by the following reaction sequence: (1) conversion of cyclohexanone to 2‐allycyelohexanone by reaction wtih allyl bromide and sodium amide and (2) conversion of 2‐allycyclohexanone to the desired monomer by reaction with the phosphorane derived from methyltriphenylphosphonium bromide. Polymerizaton was accomplished by use of boron trifluoride resulting in 44% conversion to polymer, of which 94% was soluble. Through use of infrared and nuclear magnetic resonance techniques, the soluble portion of the polymer was shown to contain 54% of bicyclic units and the remainder to be non‐cyelized monomer units in which the residual unsaturation was composed predominantly of allyl groups.