Synthesis of self-curable polysulfone containing pendant benzoxazine units via CuAAC click chemistry

Abstract

Synthesis, characterization, and properties of new thermally curable polysulfone containing benzoxazine moieties in the side chain were investigated. First, chloromethylation and subsequent azidation processes were performed to form polysulfone containing pendant clickable azide groups. Independently, antagonist 3,4-dihydro-3-(prop-2-ynyl)-2H-benzoxazine was prepared by using paraformaldehyde, phenol and propargylamine. The following copper(I) catalyzed azide-alkyne cycloaddition click reaction was applied to obtain self-curable polysulfone with pendant benzoxazine units. The polymer and intermediates at various stages were characterized by 1H-NMR, 13C-NMR and FT-IR spectroscopies. The thermal properties and curing behavior of final polymer were investigated by differential scanning calorimetry and thermal gravimetric analysis. Compared to the neat polysulfone, the obtained polymers exhibited thermally more stable polymers.

Synthesis, characterization and surface properties of star-shaped polymeric surfactants with polyhedral oligomeric silsesquioxane core

“…In particular Cu(I)‐catalysed 1,3‐dipolar Huisgen cycloaddition (CuAAC) reaction between azide and alkyne functional groups has attracted considerable attention due to the high yield and applicability under mild reaction conditions . This reaction has been widely used for the fabrication of various organic and hybrid complex macromolecular structures …”

3,4-Dihydro-2H-1,3-benzoxazines and their oxo-derivatives - Chemistry and bioactivities

“…thermal stability, durability in harsh conditions, oxidation, pH and temperature resistance, ease of process ability and good film properties. 69,70 Sulfone-scaffold 3.4-Dihydro-2H-1,3-benzoxazines (6) were prepared in high purity from 4,4′-diaminodiphenyl sulfone (7), 71,72 bisphenolsulfone (8) 25 or polysufone 73 and paraformaldehyde and phenol using high boiling point nonpolar solvent. See Figure 4.…”

A new cardo bisphenol monomer containing pendant azido group and the resulting aromatic polyesters

“…With regard to step‐growth polymers, both postfunctionalization and functional monomer approaches have been put to use to obtain a range of azido‐functionalized aliphatic and aromatic polymers. The prominent examples of such polymeric systems include polycarbonates, polyesters, polyurethanes, polyamides, poly(ether sulfone)s, and poly(ether ether ketone)s . As far as functional monomer approach is concerned, most of the reports deal with aliphatic polymers and relatively lesser attention has been paid to monomers suitable for the synthesis of aromatic step‐growth polymers …”