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Synthesis and ring‐opening polymerization of α ‐chloromethyl‐ α ‐methyl‐ β ‐propiolactone
Author(s) -
Liu XiangQian,
Wang MingXia,
Li ZiChen,
Li FuMian
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(19990201)200:2<468::aid-macp468>3.0.co;2-n
Subject(s) - polymerization , chemistry , polymer chemistry , crystallinity , pyridine , triethylamine , trifluoroacetic acid , ring opening polymerization , organic chemistry , polymer , crystallography
α ‐Chloromethyl‐ α ‐methyl‐ β ‐propiolactone (CMMPL) was synthesized by dehydrohalogenation of α , α ‐dichloromethyl‐ β ‐propionic acid which was obtained by chlorination of α , α ‐hydroxymethyl‐ β ‐propionic acid (DMPA). Due to high strain of the four‐numbered ring, CMMPL can be polymerized by ring‐opening with or without an initiator. Both electrophiles like trifluoroacetic acid (TFAA) and nucleophiles like triethylamine (TEA) and pyridine, as well as organometallic compounds such as stannous octoate [Sn(Oct) 2 )], aluminium triisopropoxide [Al(O i Pr) 3 ] and tetrabutyl orthotitanate [Ti(OC 4 H 9 ) 4 ], were found to be effective initiators. The polymerization can be conducted by either solution or bulk polymerization. P(CMMPL) is insoluble in almost all organic solvents at room temperature. An endothermic peak (ca. 214 ˜ 250°C) attributed to the melting transition of P(CMMPL) was observed in DSC curves. P(CMMPL) tends to have high crystallinity (40% ˜ 60%) as demonstrated by its X‐ray diffraction patterns, and the crystallinity was found to vary with the types of initiator used.