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Preparation and properties of polymers of secondary alkyl crotonates and related monomers
Author(s) -
Graham Roger K.,
Moore James E.,
Powell John A.
Publication year - 1967
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1967.070110916
Subject(s) - isopropyl , materials science , polymer chemistry , monomer , alkyl , polymer , polymerization , crystallinity , tacticity , tetrahydrofuran , composite material , chemistry , organic chemistry , solvent
The anionic polymerization of a variety of secondary alkyl crotonates and related monomers initiated by fluorenyllithium (complexed with tetrahydrofuran) in toluene at −78°C. is reported. No crystallinity could be developed in any of the samples, and nuclear magnetic resonance was uniformative about possible tacticity. The polymerization techniques were ineffective when applied to n ‐alkyl esters. Polymer was obtained from isopropyl cinnamate and N , N ‐dimethyl crotonamide, but not from isopropyl thiocrotonate or isopropyl 2‐pentenoate. The physical properties of injectionmolded specimens of polymers of isopropyl, s ‐butyl and cyclohexyl crotonate were examined in some detail; the polymers exhibited a desirable combination of high service temperatures and good impact resistance for a vinyl homopolymer but were extremely difficult to mold. Poly(isopropyl crotonate) had a heat distortion temperature of 125°C. at 85 psi, a notched Izod impact of 2.4 ft.‐lb./in. of notch, and a flexural modulus of 274,000 psi.