FUNCTIONALIZATION AND CROSS-LINKING REACTIONS OF ETHYL-ALPHA-HYDROXYMETHYLACRYLATE

Ethyl-alpha-hydroxymethylacrylate (EHMA) was esterified with hexanoyl chloride in 80% yield. The homopolymer of the hexanoate ester was foun d to be a glassy thermoplastic and soluble polymer. Copolymerization o f the hexanoate ester with EHMA in varying ratios gave polymers that w ere thermoplastic and more soluble as a result of internal lubrication of the long alkyl pendant groups. Copolymers with styrene were synthe sized with relatively high conversion. Reaction of EHMA with adipoyl c hloride gave a bis-ester which served as crosslinking agent when copol ymerized with different monomers including EHMA itself In a separate s ynthesis EHMA was reacted with toluenediisocyanate (TDI). In the absen ce of catalyst a monourethane was formed. This monomer still contains one isocyanate function and is capable of further reactions subsequent to double bond addition polymerization. This reaction was also carrie d out on poly-EHMA, with or without catalyst. The products were the mo no and the crosslinked bisurethanes as expected. Thus, acyl chlorides and isocyanates were found to be excellent reagents for derivatization of EHMA. (C) 1993 John Wiley & Sons, Inc.