New Functional Acrylates

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This research deals with the chemistry of alpha- hydroxymethylacrylate (HMA) ester synthesis, polymerization, and characterization. Extension and exploration of the rich chemistry of various alkyl esters (RHMAs) will make available polymerizable derivatives possessing halide, ester, ether, silyl ether, urethane, and amine groups. Many of these will also possess siloxane, hydrocarbon, and fluorocarbon residues. Reactive oligomers with internal and terminal groups will be synthesized using a newly- discovered ether-forming reaction of the RHMA alcohol groups. Also available will be monomers with supernucleophilic catalyst groups, and monomers capable of forming polymerizable micelles, vesicles, monolayers, and liquid crystalline states. Cyclopolymerization of the ether dimers generates pyran-containing polymers with pendent carboxylate groups with potential anticancer and antiviral activity. Formation of reactive halides and isocyanates of the RHMA's extends the functional capability of the monomers and polymers to many other derivatives. Anionic and group transfer polymerizations of ethers and silyl ethers will allow isotactic and controlled MW polymer formation. Studies will also deal with intramolecular 6-membered ring hydrogen bond effects on polymer solubility and physical properties, steric inhibition of polymerization by a-methyl substituents, and use of the t-butyl effect to form high molecular weight cyclopolymers.