Wydział Chemii

Magdalena Stępień

Edyta Nizioł

Małgorzata Gazińska

Aleksandra Marszałek-Harych

Wiktor Zierkiewicz

Łukasz John

Patrycja Wytrych

Jolanta Ejfler

2025

Macromolecules

58

473-487

10.1021/acs.macromol.4c01664

Naukowa

Angielski

Artykuł

A monofunctional benzoxazine with an ortho-positioned hydroxy group was designed in an attempt to obtain low-curing monomers impelled by intra- and intermolecular hydrogen bonds. A set of hydroxybenzoxazines (_OHBx^R) was synthesized with different substituents (R) on the nitrogen atom of the heterocyclic ring. The structure in the solid state indicates dimeric compounds in which benzoxazine molecules are bonded together by intermolecular hydrogen bonds between the hydroxyl functional and nitrogen atoms. All hydroxybenzoxazines showed lower curing temperatures in comparison with adequate benzoxazine monomers without hydroxy functionalization (_OHBx^R < _tBuBx^R). The ring-opening polymerization for hydroxybenzoxazines proceeds via different pathways stimulated by hydrogen bonds, giving rise to a new, unknown hydroxy-acetal type of polybenzoxazine. The crucial new stage in the modified structure of the polymer chain involves proton transfer from the hydroxy group to the activated oxygen atom from the open oxazine ring.

Aromatic compounds, Molecular structure, Monomers, Noncovalent interactions, Ring-opening polymerization

http://dx.doi.org/10.1021/acs.macromol.4c01664

https://www.acs.org/content/acs/en.html