Effect of S-triazine Ring Substitution on the Synthesis of Organic Resorcinol-Formaldehyde Xerogels

Abstract

Resorcinol (R) and formaldehyde (F) gel synthesis has been well-studied along with alternative reagents. We present the synthesis of formaldehyde-based xerogels using chemically similar s-triazine precursors, with comparison to traditional analogues. The substitution ranges from tri-hydroxyl to tri-amine, with an intermediate species, allowing changing chemistry to be investigated. Each molecule (X) offers different acid/base properties, known to influence gel formation, as well as differences in crosslinking potential. Varying X/F ratios were selected to recreate the stoichiometry used in RF systems, where one represented higher F to match the increased reaction sites of the additives. X/C ratios were selected to probe different catalyst (C) ratios, while working within the range likely to produce viable gels. Results obtained show little impact for ammeline as an additive due to its similarity to resorcinol (activation sites and pKa); while melamine and cyanuric acid show differing behavior depending on the level of addition. Low concentrations show melamine to have the most impact due to increased activation and competition for formaldehyde; while at high concentrations, cyanuric acid is shown to have the greatest impact as it creates a more acidic environment, which diminishes textural character, possibly attributable to larger clusters and/or weaker cross-linking of the system.

Editorial for Gels 6th Anniversary Special Issue

“…Xerogels are gels that retain their porous structure after drying at ambient condition. In this regard, Prostredny et al [1] investigate the impact of replacing resorcinol in resorcinol-formaldehyde gels with s-triazine precursors on the crosslinking and texture of the resulting xerogels. The substitution of the z-triazine precursor ranging from tri-hydroxyl to tri-amine allows changing the chemistry and acid-base properties of the gelation reaction.…”