Preparation and Complex Formation of Polymers Anchoring 2-Oxazolidinone

Abstract

Polymers anchoring 3-unsubstituted 2-oxazolidinone were prepared and their complex formation with phenol and mercury(II) acetate were investigated. Preformed poly(4-hydroxystyrene) was treated with tris(2,3-epoxypropyl) isocyanurate to give a polymer containing 2-oxazolidinone residues within the limits of 57.7 mol%. Polymers carrying 2-oxazolidinone were also prepared through the homopolymerization and copolymerization of 4-(2-oxo-5-oxazolidinylmethoxy)phenyl acrylate. The effective concentration of 2-oxazolidinone residue in the polymers, which is accessible to phenol, was determined on the assumption that the polymer-bound 2-oxazolidinone and phenol formed a 1 : 1 complex. 2-Oxazolidinone and a mercury atom formed a 2 : 1 complex; this relation on the molar ratio applies to all forms of complexes between the mercury atom and the 2-oxazolidinone residue in the polymers.

Stereospecific radical polymerization of methacrylate bearing oxazolidone structure and improvement of glass transition temperature of urethane methacrylate copolymers

“…A strategy for the molecular design of monofunctional monomers that impart high heat resistance to the generated polymers is the introduction of bicyclo or heterocyclic structures. [17][18][19][20][21][22][23] On the other hand, one way to improve the heat resistance of polymethacrylates is to control the stereoregularity of the main chain. [24][25][26] For example, the glass transition temperature of polymethyl methacrylate (PMMA) varies widely due to differences in stereoregularity, with syndiotactic PMMA showing the highest glass transition temperature compared to isotactic and atactic PMMA.…”

“…31 Although there have been reports on the radical polymerization behavior of N-vinyl oxazolidone and acrylates with 2-or 4-substituted oxazolidone, there are nothing studies about the radical polymerization of methacrylates with 4-substituted oxazolidone and their stereoregularity and thermal properties. 22,23 If the polymer synthesized by radical polymerization of methacrylate monomer derived from 4-substituted oxazolidone is syndiotactic rich, we thought the obtained polymers would exhibit excellent heat resistance due to the effects of the stereoregular structure in the main chain and the heterocyclic skeleton in the side chain. In this study, we synthesized a novel methacrylic monomer having an oxazolidone structure (M1) and performed the structural and thermal analysis of the polymer obtained by radical polymerization.…”

“…Therefore, we need monofunctional monomers with excellent heat resistance to obtain cured products that retain excellent thermal and mechanical properties even when less amount of the multifunctional monomers. A strategy for the molecular design of monofunctional monomers that impart high heat resistance to the generated polymers is the introduction of bicyclo or heterocyclic structures 17–23 . On the other hand, one way to improve the heat resistance of polymethacrylates is to control the stereoregularity of the main chain 24–26 .…”

“…We reported recently that glycidyl carbamate derivatives readily underwent an intramolecular cyclization with a catalytic amount of 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD) at room temperature, yielding the corresponding 4‐hydroxymethyl oxazolidines 31 . Although there have been reports on the radical polymerization behavior of N ‐vinyl oxazolidone and acrylates with 2‐ or 4‐substituted oxazolidone, there are nothing studies about the radical polymerization of methacrylates with 4‐substituted oxazolidone and their stereoregularity and thermal properties 22,23 . If the polymer synthesized by radical polymerization of methacrylate monomer derived from 4‐substituted oxazolidone is syndiotactic rich, we thought the obtained polymers would exhibit excellent heat resistance due to the effects of the stereoregular structure in the main chain and the heterocyclic skeleton in the side chain.…”

Polymerization behavior of novel vinyl monomers containing pyrrolidone moieties

“…Figure5. Change of -NMR chemical shift of PS by addition of styrene derivatives in benzene-de (PS or OS-St, PS or OS-PMS) or acetonitrile-da (PS or OS-MHS) ([C] = 0.5 mol/L).…”