Synthesis and Characterization of Low-Cost Cresol-Based Benzoxazine Resins as Potential Binders in Abrasive Composites

Artur Jamrozik; Mateusz Barczewski; Grzegorz Framski; Daniel Baranowski; Paulina Jakubowska; Łukasz Klapiszewski; Teofil Jesionowski; Adam Voelkel; Beata Strzemiecka

doi:10.3390/ma13132995

Synthesis and Characterization of Low-Cost Cresol-Based Benzoxazine Resins as Potential Binders in Abrasive Composites

Materials (Basel). 2020 Jul 5;13(13):2995. doi: 10.3390/ma13132995.

Authors

Artur Jamrozik¹, Mateusz Barczewski², Grzegorz Framski³, Daniel Baranowski³, Paulina Jakubowska¹, Łukasz Klapiszewski¹, Teofil Jesionowski¹, Adam Voelkel¹, Beata Strzemiecka¹

Affiliations

¹ Institute of Chemical Technology and Engineering, Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, PL-60965 Poznan, Poland.
² Institute of Materials Technology, Faculty of Mechanical Engineering, Poznan University of Technology, Piotrowo 3, PL-61138 Poznan, Poland.
³ Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, PL-61704 Poznan, Poland.

Abstract

A series of cresol-based benzoxazines were synthesized for potential application as a polymer matrix in abrasive composites. The chemical structures of the obtained benzoxazine resins were investigated in detail using Fourier transform infrared spectroscopy (FTIR) and hydrogen-1 as well as carbon-13 nuclear magnetic resonance spectroscopy (¹H NMR, ¹³C NMR) with an additional analysis using two-dimensional NMR techniques (2D NMR ¹H-¹H COSY, ¹H-¹³C gHSQC and gHMBC). Structural analysis confirmed the presence of vibrations of -O-C-N- at ~950 cm^-1 wavenumber, characteristic for an oxazine ring. The thermal properties of benzoxazine monomers were examined using differential scanning calorimetry (DSC) analysis. The polymerization enthalpy varied from 143.2 J/g to 287.8 J/g. Thermal stability of cresol-based benzoxazines was determined using thermogravimetry (TGA) analysis with additional analysis of the amount of volatile organic compounds (VOC) emitted from the synthesized benzoxazines during their crosslinking by static headspace coupled with gas chromatography technique (HS-GC). The amount of residual mass significantly differed between all synthesized polybenzoxazines in the range from 8.4% to 21.2%. The total VOC emission for benzoxazines decreased by 46-77% in reference to a conventional phenolic binder. The efficiency of abrasive composites with the benzoxazine matrix was evaluated based on abrasion tests. Performed analyses confirmed successful synthesis and proper chemical structure of cresol-based benzoxazines. All the experiments indicated that benzoxazines based on different cresol isomers significantly differ from each other. Good thermal performance and stability of the abrasive composites with the polybenzoxazine matrix and significantly lower VOC emission allow us to state that benzoxazines can be a promising and valuable alternative to the phenolics and a new path for the development of modern, eco-friendly abrasives.

Keywords: abrasive composites; benzoxazine resins; bonding; grinding; phenolic resins.

Grants and funding

UMO-2017/25/N/ST8/00401/Narodowe Centrum Nauki